CC BY
29
UDC 547.655.1:547.233.2
DOI: 10.18698/1812-3368-2021-1-126-143
AMINOMETHYLATED HYDROXINAPHTHALENES: SYNTHESIS AND APPLICATION
P.V. Slitikov1 Yu.B. Evdokimenkova2
pvs@bmstu.ru
1 Bauman Moscow State Technical University, Moscow, Russian Federation
2 Library of Natural Sciences, Russian Academy of Sciences, Moscow, Russian Federation
Abstract
The analysis of the literature is carried out and the results of the synthetic approaches to the aminomethylation of hydroxy derivatives of naphthalenes developed over the past 20 years are presented. Most of the described aminomethylation processes proceed as Mannich aminomethylation or, as a special case of a similar condensation — aminobenzylation according to Betti. The results of all studies are grouped according to the nature of the amine used in the synthesis: primary, secondary, tertiary. Most of the examples were considered for 2-naphthol, however, as the analysis of literature data shows, similar methods are applicable to 1-naphthol and dihydroxynaphthalenes with different positions of OH groups in the ring — often only the yields of the target product differ. Both the classical methods for the preparation of Mannich and Betti bases using the carbonyl component (formaldehyde, benzaldehyde and its derivatives, respectively) and special cases of synthesis, in which condensation is carried out by means of halogen derivatives, substituted azacrown ethers, etc., are presented. Particular attention is paid to the use of various catalysts and activators, allowing to significantly simplify the synthetic procedures and increase the yields of target compounds. The main fields of application of amino-methylated derivatives of hydroxynaphthalenes are presented
Keywords
Mannich aminomethylation, Betti aminobenzylation, primary amines, secondary amines, formaldehyde, 2-naphthol, dihydroxynaphthalenes
Received 09.08.2020 Accepted 20.10.2020 © Author(s), 2021
Introduction. Since its discovery, the Mannich reaction [1] and Betti [2] reactions have been widely used in organic synthesis among the most convenient ways to create C-C bonds, which are also applicable for the series of condensed aromatic derivatives. Currently, aminomethylation has been
fairly well studied on 2-naphthol (P-naphthol), and in the last 20 years, a large number of studies have also appeared on the introduction of aminomethyl fragments into 1-naphthol (a-naphthol) and dihydroxynaphthalenes. It is known that the presence of aminomethyl groups in the structure of the molecules, especially those containing a heterocyclic fragment, leads to an increase in the physiological activity of the product [3-6]. Most often, aminomethylated derivatives of naphthalene systems are used as starting compounds of fine organic synthesis for the production of physiologically active substances [7-11], in the synthesis of homoisobioflavonoids [12], chromenes [13, 14], flavonoid analogues — enzyme inhibitors showing high activity [15-17], in the development of drugs with antiparasitic properties [18], new water-soluble inhibitors of tumor cell proliferation [19], ligands for the creation of complexes that are effective catalysts [20, 21] and contrasts in magnetic resonance imaging [22], as well as tautomeric switches [23].
Aminomethylation using primary amines. In most cases, the introduction of primary amines into aminomethylation pursues the goal of forming a six-membered oxazine ring with a functional substituent [24, 25]. Condensation of 2-naphthol 1 and formaldehyde with primary diamines 2a-c at a reagent ratio of 2: 4: 1 yielded naphthoxazines 3a,b, which, upon further interaction with 2-naphthol 1, formed aminomethylated derivatives 4a-c containing four residues of 2-naphthol in their structure [26]:
4a-c
In case 3a, b, the reaction proceeded in refluxing in methanol for 1 h with a yield of about 45 %, while 3c was synthesized in 5 % yield in methanol with cooling. Further interaction of all naphthoxazines 3а-c with 2-naphthol 1 proceeded at room temperature.
In general, the interaction of naphthoxazine derivatives with naphthols is a fairly common synthetic technique which was used previously for the synthesis of different compounds [27, 28]. The opening of the oxazine ring can also be
carried out by reaction with trimethylsilyl triilate by heating in toluene in the presence of tertiary amines [29].
The work [30] describes the preference of tyramines (P-(4-hydroxyphenyl) ethylamines) to bind with 2-naphthol 1 rather than undergo self-condensation.
This experimental fact is explained using semi-empirical and non-empirical calculations for complexes of so-called "macrocyclic templates" based on hydrogen bonds formed in solution as a transition state, in which 2-naphthol behaves as the most active reagent.
The reaction of 1,6-dihydroxynaphthalene with primary aromatic amines leads to dioxazines 7 [31] and 8 [32], and the closure of the oxazine ring occurs not in the fifth, but in the seventh position of the naphthalene ring.
Aminomethylation of 1,6-dihydroxynaphthalene is carried out under harsher conditions than in the case of 2-naphthol 1 or 2,7-dihydroxynaphtha-lene.
Condensation of 1- and 2-naphthol, as well as various dihydroxynaphtha-lenes 9a-c bearing remote OH-groups with monoaminotetraphenylporphyrin and formaldehyde, makes it possible to obtain various oxazinoporphyrins. Reactions proceed when boiling in THF for 24-30 h with yields of ~ 90 % (for mon-ohydroxynaphthalenes) and ~ 40 % (for dihydroxynaphthalenes) [33].
It should be noted that in the case of 1,6-dihydroxynaphthalene 9b in the reaction product 10b, the oxazine ring closes to the fifth and sixth positions, in contrast to the results described in [34, 35].
Aminomethylation using secondary amines. Despite the popularity of primary amines and the possibility of creating condensed rings on their basis, in most methods of aminomethylation of hydroxynaphthalene derivatives (1- and 2-naphthol, dihydroxynaphthalenes), various secondary amines of both aliphatic and heterocyclic series have been used over the past 20 years: dimethylamine [3436], diethyl- and dibutylamines [37], dibenzylamine [37, 38], methylbenzylamine [38], heterocyclic pyrrolidine, piperidine, morpholine [37], piperazine [36, 39], amino acids [40], as well as amines containing complex substituents [20, 30]. In most cases, the reactions proceed at room temperature [30, 34-36, 38] or at the boiling point of solvents [20, 37, 39, 40], which are various alcohols, dichloro-methane, and water. Aminomethylated products (Mannich bases) are formed in good yields (~ 80-95 %). Examples of reactions proceeding with 2-naphthol 1 are given below:
HO'
Oi
11
Л = 21-73 %
The processes listed above are also possible for 1-naphthol [35, 37, 38], but the yields of target products based on it, as a rule, are lower than those for 2-naphthol.
Dihydroxynaphthalenes (9c-f) can undergo both mono- and bisaminometh-ylation. 2,6-(9d), 2,7-(9c), and 1,3-(9f) Dihydroxynaphthalenes were introduced into the Mannich reaction, where dibutylamine, piperidine, and morpholine were used as the amine component. The reactions proceeded in methanol at room temperature [41-43].
,1:1 = 1,CH,OH, UO-fY\ -2H20 "^V^nil
In the case of cyclic amines, the reaction rate and product yield were much higher (> 80 %) than with dibutylamine. The yields of monoaminomethylated analogs 13 were slightly lower than their bisaminomethylated derivatives 14a-c (> 80 % and > 92 %, respectively). It was noted that at any 1,3-dihydro-xynaphthalene: formaldehyde: amine ratios, no monoaminomethylated derivatives were formed, which is probably due to the high reactivity of the hydrogen atoms of the aromatic ring at positions 2 and 4.
Using a similar procedure with diamines such as N,N'-dimethyl-and N,N'-dibenzylethylenediamines, N,N'-diethyl-1,3-propylenediamine and piperazine Mannich bases 15 were obtained in high yields (> 95 %), each containing two functionalized aromatic fragments — either 2-naphthol 1 or 2,7-dihydroxynaphthalene 9c [44].
OH HO
1,9c
H
Л
R' R R'
1H NMR and IR spectra of derivatives 13 and 15 were affected by the intramolecular hydrogen bond O-H—N: at t = 22 °C, the 1H NMR spectrum showed broadening of the signals of the protons of the piperidine, morpholine, or piperazine rings, respectively (2 in Fig. 1 a); however, when the sample was heated to t = 80 °C (d-DMSO), a narrow signal from the indicated protons appeared in the 1H NMR spectrum, since at this temperature the hydrogen bond was broken (2 in Fig. 1 b).
3 2
a b
Fig. 1. Fragment of 'H NMR spectrum (400 MHz, d-DMSO) of 1-morpholinomethyl-2,7-dihydroxynaphthalene 13, recorded at:
a) t = 22 °C; b) t = 80 °C [43]
It is noted that bisaminomethylated dihydroxynaphthalenes bearing heterocyclic substituents demonstrate extremely low solubility in organic solvents (dioxane, acetonitrile, chloroform).
1,5- [35] and 2,3- [38] Dihydroxynaphthalenes were also subjected to bis-aminomethylation, but the yields of the target products were lower than those of the aforementioned analogs.
In a number of studies, microwave irradiation was also used to intensify the process of introducing an aminomethyl group into the naphthalene ring [4, 34, 45]. The reactions were carried out without solvent and in the presence of p-toluenesulfonic acid as a catalyst; however, the yields of the target products were comparable to the classical methods. An undoubted advantage of this synthesis can be considered a significant reduction in the reaction time (from several hours to several minutes).
As can be seen, in all the described cases, formaldehyde was used as the car-bonyl component. When the latter is replaced by an aromatic aldehyde, an ami-noarylation reaction or Betti condensation takes place. Thus, the interaction of 2-naphthol 1 with secondary amines of various nature in the presence of aromatic aldehydes in a glycerol medium at a temperature of 90 °C [36], a water-ethanol mixture at room temperature [46] or under the action of microwave radiation (« 1 min) and the use of p-toluenesulfonic acid as a catalyst [45, 47] leads to the formation of derivatives 16:
R =
The yields of products 16 were in the range of 72-86 % depending on R.
Figure 2 shows the molecular structure of one of the products of the described condensation, where N-methylpiperazine was used as the amine component. X-ray diffraction analysis showed the presence of O-H--N hydrogen bonds, which stabilize the general configuration of the molecule, as was already noted for monoaminomethylated derivatives of dihydroxynaphthalenes [41-44].
The Mannich and Betti reactions can be carried out without using a solvent. For example, heating the mixture of 2-naphthol 1, formaldehyde or benzaldehyde with various amines up to 60 °C for 1,5-2 h together with MgSO4 [48] or at 40 °C for ~ 30 min using a heterogeneous catalyst nano-SiO2-H3BO3 [49] yielded products 11, 12, 16. The yields of the indicated
Fig. 2. Molecular structure of derivative 16 (R = Ph, NR2 = N-methylpiperazine) [47]
derivatives in the first case are comparable with the previously considered methods, while the product yields when using the nano-SiO2-H3BO3 catalyst are always higher than 90 %.
Tertiary amines. Special cases of aminomethylation. The introduction of selective catalysts into the sphere of reaction or the presence of specific leaving groups in the starting materials make it possible to introduce tertiary amines into aminomethylation without using carbonyl derivatives. In the presence of catalytic amounts of Au(III) salts and CCbBr as an initiator, selective oxidative aminomethylation of 2-naphthol 1 with tertiary amines occurs at room temperature [50]:
Me I
Л = 37 % ti = 8 %
In this case, a mixture of Mannich base with naphthoxazine is formed, and the yields of both are low.
Higher yields (72-80 %) of naphthalenes 17 selectively aminomethylated in o-position to OH-groups were obtained from 2-naphthol and its am-phiphilic derivatives upon their oxidative heterogeneous coupling with tertiary amines in the presence of Cu7S4 nanoparticles [51].
X = H, OMe,Br R = H, o, m, p-C\
Product 17 (X = H, R = H) was also obtained via 2-naphthylboronic acid [52]. The reaction proceeded in water at 90 °C in the presence of f-BuOOH and NiCl2 as a catalyst for 12 h with a yield of 74 %.
The use of triethylsiloxymethylamine (Et3SiOCH2NMe2) also makes it possible to carry out aminomethylation without the participation of the carbonyl component with the formation of derivatives 11 [53]. The process takes place in benzene at room temperature for 20 min, but the yields with this synthesis method are much lower (57-73 %).
Environmentally friendly synthesis with the use of pincer complexes of Mn(I) [54] and Re(I) [55] involves the use methanol instead of aldehydes to obtain derivatives 11, 12 and 16. This process takes place in toluene at 120-130 °C for 16 h, and the product yields are either lower or comparable to the previously considered examples.
In the Mannich reaction, azacrown ethers can also be used as the amine component [3, 56, 57]. In this case, the process is also carried out without the participation of a carbonyl compound, using transesterification on graphite [3] or in a toluene solution [56] with strong heating:
In the first case, the yield of target products 18, depending on the aromatic substituent (1- or 2-naphthols, hydroxyquinolines, substituted phenols) was 7592 %, and in the second derivative 19 — only 74 %.
As already noted, in addition to formaldehyde, dichloro- and dibromo-methane can act as methylating reagents [57, 58]. When this reaction was carried out at room temperature, the yield of product 20 based on 2-naphthol was 74 %. Depending on the starting naphthol, when mono- (11, 21) or diamino-methylated (22) products are heated to 110 °C, either 2,2'-dihydroxy-1,1'-dinaph-thylmethane 23 or bisaminomethylated dinaphthylmethane derivative 24 can be obtained in 76 %.
The use of vanadium (IV) and (V) salts as catalysts makes it possible to carry out aminomethylation of 1- and 2-naphthol with amine N-oxides with the formation of derivatives 12 and 21 with good yields (58-92 %) [59]. The best results were shown by VO(acac)2 (yield 92 % for 8 h of reflux in CH2O2, R = morpholine).
Similarly, the use of dimethylmethyleneimine iodide in the interaction with 2-naphthol 1 in the presence of the Et3N-MgCl2 system in CH2Q2 gives derivative 11 (R = Me) in quantitative yield [60].
The use of benzotriazoles, as an easily leaving group, allows the introduction of an aminomethyl fragment (derivatives of substituted tetra-hydroisoquinoline) into the 2-naphthol 1 also without using the carbonyl component [61]. The process takes place for 24 h in boiling chloroform with the yield of the target product 25 over 90 %.
Aminomethylation with tetraazatricyclododecane (TATD) 26 and other polycyclic amines proceeds similarly without the use of carbonyl compounds [62-66]. For example, TATD reacts with 2-naphthol 1 under mild conditions: room temperature, water-dioxane solution, 1 day:
In the works it is noted that one of the key moments of such condensation is the activity of the a-protons of the naphthalene ring.
It was shown that such a reaction does not occur with the dibenzo analogue TATD 26. A similar behavior is observed with bis(benzotriazoimidazoles): the reaction products are monoaminomethylated products 27 (Fig. 3) with a yield of no more than 47 % [63, 64]. Such reactions take place when heated in alcohols for several hours. Studying derivatives 27 by X-ray diffraction analysis showed the existence of strong intermolecular hydrogen bonds and the absence of intramolecular ones, as was noted in [41, 42, 44, 45, 47].
Conclusion. The processes of aminomethylation and aminobenzylation continue to be relevant and popular methods for creating C-C bonds in a series of condensed aromatic systems. With the development of synthetic approaches, the yields of the target products increase, the conditions become softer due to
1 +
N' 26
Fig. 3. Molecular structure of compound 27 [63]
the use of catalysts or the selection of appropriate solvents. At the same time, there is a constant and quite natural expansion of the areas of application of the Mannich and Betti bases.
Translated by A.G. Martynov
REFERENCES
[1] Mannich C., Krösche W. Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak und Antipyrin. Arch. Pharm., 1912, art. 250, no. 1, pp. 647-667.
DOI: https://doi.org/10.1002/ardp. 19122500151
[2] Betti M. ß-Naphthol phenilaminomethane. Org. Syntheses, 1929, vol. 9, pp. 60. DOI: https://doi.org/10.1002/0471264180.os009.21
[3] Sharghi H., Khalifeh R., Salimi Beni A.R. Synthesis of new lariat ethers containing polycyclic phenols and heterocyclic aromatic compound on graphite surface via Mannich reaction. J. Iran. Chem. Soc., 2010, vol. 7, no. 1, pp. 275-288.
DOI: https://doi.org/10.1007/BF03245889
[4] Mojtahedi M.M., Sharifi A., Mohsenzadeh F., et al. Microwave-assisted aminomethylation of electron-rich compounds under solvent-free condition. Synth. Commun., 2000, vol. 30, iss. 1, pp. 69-72. DOI: https://doi.org/10.1080/00397910008087294
[5] Rogovsky V.S., Arzamasova T.M., Rosenfel'd M.A., et al. Effect of an inclusion complex of an aminomethylated dihydroquercetin derivative in cyclodextrin on ozone-induced oxidation of fibrinogen. Pharm. Chem. J., 2013, vol. 47, no 6, pp. 295-295. DOI: https://doi.org/10.1007/s11094-013-0946-x
[6] Shi Y., Wang O., Gao S. Recent advances in the intromolecular Mannich reaction in nature products total synthesis. Org. Chem. Front., 2018, vol. 5, iss. 6, pp. 1049-1066. DOI: https://doi.org/10.1039/C7QO01079F
[7] Lukashenko A.V., Osipov D.V., Osyanin V.A., et al. The reaction of 1,2-naphtho-quinone 1-methides with syncarpic acid. Chem. Heterocycl. Comp., 2019, vol. 55, no. 10, pp. 1004-1006. DOI: https://doi.org/10.1007/s10593-019-02569-4
[8] Korzhenko K.S., Osipov D.V., Osyanin V.A., et al. Reaction of cross-conjugated push-pull enamino ketones with 1,2-naphthoquinone 1-methides: synthesis of 3-aryl-1-(1H-benzo[/]chromen-2-yl)prop-2-en-1-ones. Chem. Heterocyc. Comp., 2018, vol. 54, no 10, pp. 940-945. DOI: https://doi.org/10.1007/s10593-018-2377-9
[9] Lukashenko A.V., Osyanin V.A., Osipov D.V., et al. Reaction of push-pull enami-noketones and in situ generated ortho-quinone methides: synthesis of 3-acyl-4H-chromenes and 2-acyl-1H-benzo[/]chromenes as precursors for hydroxybenzylated het-erocycles. J. Org. Chem., 2017, vol. 82, iss. 3, pp. 1517-1528.
DOI: https://doi.org/10.1021/acs.joc.6b02716
[10] Lukashenko A.V., Osipov D.V., Osyanin V.A., et al. Reactions of 1-[(dimethyla-mino)methyl]naphthalen-2-ols with cyclic push-pull nitroenamines. Chem. Heterocyc. Comp., 2017, vol. 53, no 12, pp. 1369-1372.
DOI: https://doi.org/10.1007/s10593-018-2219-9
[11] Slitikov P.V., Rasadkina E.N. Phosphorylation of aminomethylated derivatives of 2,7-dihydroxynaphthalenes. Russ. J. Gen. Chem, 2016, vol. 86, no. 3, pp. 544-550. DOI: https://doi.org/10.1134/S1070363216030099
[12] Mrug G.P., Myshko N.V., Bondarenko S.P., et al. One-pot synthesis of B-ring or-tho-hydroxylated sappanin-type homoisoflavonoids. J. Org. Chem., 2019, vol. 84, iss. 11, pp. 7138-7147. DOI: https://doi.org/10.1021/acs.joc.9b00814
[13] Osyanin V.A., Lukashenko A.V., Osipov D.V., et al. Synthesis of 2-nitro-1H-benzo[/]chromenes. Chem. Heterocyc. Comp., 2015, vol. 50, no. 11, pp. 1528-1533. DOI: https://doi.org/10.1007/s10593-014-1620-2
[14] Ded M.L., Pegu C.D., Deka B., et al. Brensted-acid-mediated divergent reactions of Betti bases with indoles: an approach to chromeno[2,3-fr]indoles through intramolecular dehydrogenative C2-alkoxylation of indole. Eur. J. Org. Chem., 2016, vol. 2016, iss. 20, pp. 3441-3448. DOI: https://doi.org/10.1002/ejoc.201600546
[15] Spasov A.A., Badkov D.A., Osipov D.V., et al. Synthesis, in vitro and in vivo evaluation of 2-aryl-4H-chromene and 3-aryl-1H-benzo[/]chromene derivatives as novel a-glucosidase inhibitors. Bioorganic Med. Chem. Lett., 2019, vol. 29, iss. 1, pp. 119-123. DOI: https://doi.org/10.1016/j.bmcl.2018.10.018
[16] Spasov A.A., Badkov D.A., Prokhorova T.Yu., et al. Synthesis and biological evaluation of 2-acylbenzofuranes as novel a-glucosidase inhibitors with hypoglycemic activity. Chem. Biol. Drug Des., 2017, vol. 90, iss. 6, pp. 1184-1189.
DOI: https://doi.org/10.1111/cbdd. 13038
[17] Chen H.-L., Chang C.-Y., Lee H.-T., et al. Synthesis and pharmacological exploitation of clioquinol-derived copper-binding apoptosis inducers triggering reactive oxygen species generation and MAPK pathway activation. Bioorganic Med. Chem., 2009, vol. 17, iss. 20, pp. 7239-7247. DOI: https://doi.org/10.1016/jj.bmc.2009.08.054
[18] Silvestri I., Lyu H., Fata F., et al. Ectopic suicide inhibition of thioredoxin glutathione reductase. Free Radic. Biol. Med., 2020, vol. 147, pp. 200-211.
DOI: https://doi.org/10.1016/jfreeradbiomed.2019.12.019
[19] Vojacek S., Beese K., Alhalabi Z., et al. Three-component aminoalkylations yielding dihydronaphthoxazine-based sirtuin inhibitors: scaffold modification and exploration of space for polar side-chains. Arch. Pharm., 2017, vol. 350, iss. 7, special issue: Carl Mannich, art. e1700097. DOI: https://doi.org/10.1002/ardp.201700097
[20] Lei X., Chelamalla N. Dioxomolybdenum(VI) complexes with linear and tripodal tetradenate ligands: synthesis, structures and their use as olefin epoxidation catalysts. Polyhedron, 2013, vol. 49, iss. 1, pp. 244-251.
DOI: https://doi.org/10.1016/jj.poly.2012.10.022
[21] Jçdrzkiewicz D., Ejfler J., Gulia N., et al. Designing ancillary ligands for hetero-leptic/homoleptic zinc complex formation: synthesis, structures and application in ROP of lactides. Dalton Trans., 2015, vol. 44, iss. 30, pp. 13700-13715.
DOI: https://doi.org/10.1039/C5DT01553G
[22] Kuznik N., Wyskoska M., Jarosz M., et al. Amino-phenol complexes of Fe(III) as promising T1 accelerators. Arab. J. Chem., 2019, vol. 12, iss. 7, pp. 1424-1435.
DOI: https://doi.org/10.1016/j.arabjc.2014.11.009
[23] Antonov L., Deneva V., Simeonov S., et al. Exploiting tautomerism for switching and signaling. Angew. Chem. Int. Ed., 2009, vol. 48, iss. 42, pp. 7875-7878.
DOI: https://doi.org/10.1002/anie.200903301
[24] Tavlinova-Kirilova M., Marinova M., Angelova P., et al. Three component condensation of a Betti-type — efficient tool for synthesis of chiral naphthoxazines and amino-benzylnaphthols for enantioselective diethylzinc addition to aldehydes. Bulgarian Chem. Commun., 2016, vol. 48, no. 4, pp. 705-712.
[25] Osipov D.V., Osyanin V.A., Khaysanova G.D., et al. An inverse electron demand azo-diels-alder reaction of o-quinone methides and imino ethers: synthesis of benzo-condensed 1,3-oxazines. J. Org. Chem., 2018, vol. 83, iss. 8, pp. 4775-4785.
DOI: https://doi.org/10.1021/acs.joc.8b00692
[26] Woodgate P.D., Horner G.M., Maynard N.P., et al. Synthesis of dioxazaborocines from N,N'-alkylbridged-bis(bis(2-hydroxybenzyl)aminomethyl)amines. J. Organomet. Chem, 2000, vol. 595, iss. 2, pp. 215-223.
DOI: https://doi.org/10.1016/S0022-328X(99)00627-0
[27] Woodgate P.D., Horner G.M., Maynard N.P. A novel method for functionalising resorcinarenes. Tetrahedron Lett., 1999, vol. 40, iss. 35, pp. 6507-6510.
DOI: doi.org/10.1016/S0040-4039(99)01338-6
[28] Woodgate P.D., Horner G.M., Maynard N.P., et al. Synthesis of dioxazaborocines from N-substituted-bis(2-hydroxyaryl)aminomethylamines. J. Organomet. Chem., 1999, vol. 592, iss. 2, pp. 180-193. DOI: https://doi.org/10.1016/S0022-328X(99)00510-0
[29] Lery F.-X., Kunesch N., George P., et al. A new general route to novel azomethine ylides for cycloaddition reactions. Heterocycles, 2002, vol. 57, no. 9, pp. 1599-1614. DOI: https://doi.org/10.3987/COM-02-9484
[30] Díaz-Oviedo C., Quevedo R. Role of hydrogen bonding in the selectivity of aromatic Mannich reaction of tyramines: macrocyclization vs. linear condensation. J. Mol. Structure, 2020, vol. 1202, art. 127283.
DOI: https://doi.org/10.1016/j.molstruc.2019.127283
[31] Choi S., Park J. Naphthoxazine benzoxazine-based monomer, polymer thereof, electrode for fuel cell including the polymer, electrolyte membrane for fuel cell including the polymer, and fuel cell using the electrode. Patent US 2055706A1. Appl. 31.10.2008, publ. 06.05.2009.
[32] Choi S., Park J. Naphthoxazine benzoxazine-based monomer, polymer thereof, electrode for fuel cell including the polymer, electrolyte membrane for fuel cell including the polymer, and fuel cell using the electrode. Patent US 8188210B2. Appl. 29.05.2012, publ. 29.05.2012.
[33] Sharma S., Nath M. Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins. Beilstein J. Org. Chem., 2013, vol. 9, no. 3, pp. 496-502.
DOI: https://doi.org/10.3762/bjoc.9.53
[34] Matsumoto J., Ishizu M., Kawano R., et al. Generation of quinone methide from aminomethyl(hydroxy)arenes precursors in aqueous solution. Tetrahedron, 2005, vol. 61, iss. 24, pp. 5735-5740. DOI: https://doi.org/10.1016/j.tet.2005.04.037
[35] Fujiwara M., Sakamoto M., Komeyama K., et al. Convenient synthesis of 2-amino-4H-chromenes from photochemically generated o-quinone methides and malono-nitrile. J. Heterocyclic Chem., 2015, vol. 52, iss. 1, pp. 59-66.
DOI: https://doi.org/10.1002/jhet.1964
[36] Ganesan S.S., Rajendran N., Sundarakumar S.I., et al. ß-Naphthol in glycerol: a versatile pair for efficient and convenient synthesis of aminonaphthols, naphtho-1,3-oxazines, and benzoxanthenes. Synthesis, 2013, vol. 45, no. 11, pp. 1564-1568.
DOI: https://doi.org/10.1055/s-0033-1338430
[37] Arzephoni A.Y., Naimi-Jamal M.R., Sharifi A., et al. [Omim][BF4] ionic liquid, a green and recyclable medium for one-pot aminomethylation of electron-rich aromatic compounds. J. Chem. Res., 2013, vol. 37, iss. 4, pp. 216-218.
DOI: https://doi.org/10.3184%2F 174751913X13635476751996
[38] Abonia R., Castillo J., Insuasty B., et al. Efficient catalyst-free four-component synthesis of novel y-aminoethers mediated by a Mannich type reaction. ACS Comb. Sci., 2013, vol. 15, iss. 1, pp. 2-9. DOI: https://doi.org/10.1021/co300105t
[39] Mohanty S., Suresh D., Balakrishna M.S., et al. Phosphine free diamino-diol based palladium catalysts and their application in Suzuki — Miyaura cross-coupling reactions. J. Organomet. Chem., 2009, vol. 694, iss. 13, pp. 2114-2121.
DOI: https://doi.org/10.1016/j.jorganchem.2009.02.019
[40] Gawdzik B., Wakdemar I. Synthesis, structure, and stereochemistry of the bora derivatives of 1-[(2-hydroxy-1-naphthyl)methyl]proline. Tetrahedron: Asym., 2005, vol. 16, iss. 11, pp. 2019-2023. DOI: https://doi.org/10.1016/j.tetasy.2005.04.021
[41] Nifant'ev E.E., Slitikov P.V., Rasadkina E.N. Aminomethylated derivatives of 2,7-dihydroxynaphthalene. Dokl. Chem., 2014, vol. 457, no. 1, pp. 129-131.
DOI: https://doi.org/10.1134/S0012500814070052
[42] Nifant'ev E.E., Slitikov P.V., Rasadkina E.N. Bis(aminomethylation) of dihy-droxynaphthalenes. Dokl. Chem., 2015, vol. 463, no. 1, pp. 178-180.
DOI: https://doi.org/10.1134/S0012500815070046
[43] Slitikov P.V., Rasadkina E.N. Aminomethylated derivatives of 2,6-dihydro-xynaphthalene and features of their phosphorylation. ХХ Mendeleev Cong. Gen. Appl. Chem. Ekaterinburg, 2016, vol. 1, p. 326.
[44] Slitikov P.V., Rasadkina E.N. Aminomethylation of naphthalen-2-ol and naphtha-lene-2,7-diol. Russ. J. Org. Chem, 2016, vol. 52, no. 10, pp. 1432-1435.
DOI: https://doi.org/10.1134/S1070428016100109
[45] Huang P.-J.J., Cameron T.S., Jha A. Novel synthesis of 2,2-dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans. Tetrahedron Lett., 2009, vol. 50, iss. 1, pp. 51-54. DOI: https://doi.org/10.1016/j.tetlet.2008.10.083
[46] Osipov D.V., Osyanin V.A., Klimochkin Yu.N. New synthesis of 3-amino-1H-benzo[/jchromene-2-carbonitriles. Russ. J. Org. Chem., 2013, vol. 49, no. 3, pp. 398402. DOI: https://doi.org/10.1134/S1070428013030147
[47] Jha A., Nawal K.P., Trikha S., et al. Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour. Can. J. Chem, 2006, vol. 84, no. 6, pp. 843-853.
DOI: https://doi.org/10.1139/v06-081
[48] Ganesan S.S., Asaithampi G. Magnesium sulfate promoted efficient and green synthesis of aminoalkyl, amidoalkyl and diarylmethane derivatives. Asian J. Chem., 2014, vol. 26, no. 24, pp. 8380-8382.
DOI: http://dx.doi.org/10.14233/ajchem.2014.17618
[49] Teimuri-Mofrad R., Gholamhosseini-Nazari M., Esmati S., et al. An efficient and green method for the synthesis of Betti base employing nano-SiO2-H3BO3 as a novel recyclable heterogeneous catalyst. Res. Chem. Intermed., 2017, vol. 43, no. 12, pp. 68456861. DOI: https://doi.org/10.1007/s11164-017-3024-2
[50] Sun W., Lin H., Zhou W., et al. Oxidative ortho-aminomethylation of phenols via C-H and C-C bond cleavage. RCS Advances, 2014, vol. 4, iss 15, pp. 7491-7494.
DOI: https://doi.org/10.1039/C3RA46373G
[51] Gupta S., Chandna N., Dubey P., et al. GO-Cu7S4 catalyzed: ortho-amino-methylation of phenol derivatives with N,N-dimethylbenzylamines: site-selective oxidative CDC. Chem. Commun., 2018, vol. 54, no. 54, pp. 7511-7514.
DOI: https://doi.org/10.1039/C8CC03396J
[52] Kumar P., Kumar S.A., Singh R., et al. Nickel catalyzed ipso-hydroxylation and subsequent cross dehydrogenative coupling of arylboronic acids with tertiary amines: a facile access to a-phenolated tertiary amines. Adv. Synth. Catal., 2018, vol. 360, iss. 9, pp. 1786-1789. DOI: https://doi.org/10.1002/adsc.201701625
[53] Gonzalez P.E., Sharma H.K., Chakrabarty S., et al. Triethylsiloxymethyl-N,N-dimethylamine, Et3SiOCH2NMe2: a dimethylaminomethylation (Mannich) reagent for O-H, S-H, P-H and aromatic C-H Systems. Eur. J. Org. Chem., 2017, vol. 2017, iss. 37, pp. 5610-5616. DOI: https://doi.org/10.1002/ejoc.201700902
[54] Mastalir M., Pittenauer E., Allmaier G., et al. Manganese-catalyzed aminomethyla-tion of aromatic compounds with methanol as a sustainable C1 building block. J. Am. Chem. Soc., 2017, vol. 139, iss. 26, pp. 8812-8815.
DOI: https://doi.org/10.1021/jacs.7b05253
[55] Mastalir M., Glatz M., Pittenauer E., et al. Rhenium-catalyzed dehydrogenative coupling of alcohols and amines to afford nitrogen-containing aromatics and more. Org. Lett, 2019, vol. 21, iss. 4, pp. 1116-1120.
DOI: https://doi.org/10.1021/acs.orglett.9b00034
[56] Fang M., Fu E., Yuan Q., et al. A short synthesis of chiral macrocyclic dioxopoly-amines derived from L-proline. Synth. Commun., 2002, vol. 32, iss. 23, pp. 3629-3635. DOI: https://doi.org/10.1081/SCC-120014977
[57] Wu K.-C., Lin Y.-S., Yeh Y.-S., et al. Design and synthesis of intramolecular hydrogen bonding systems. Their application in metal cation sensing based on excited-state proton transfer reaction. Tetrahedron, 2004, vol. 60, iss. 51, pp. 11861-11868.
DOI: https://doi.org/10.10167j.tet.2004.09.102
[58] Hon Y.-S., Chou Yu-Yu, Wu I-C. Dibromomethane as one-carbon source in organic synthesis: the Mannich base formation from the reaction of phenolic compounds with a preheated mixture of dibromomethane and diethylamine. Synth. Commun., 2004, vol. 34, iss. 12, pp. 2253-2267.
DOI: https://doi.org/10.1081/SCC-120038509
[59] Hwang D.-R., Uang B.-J. A modified Mannich-type reaction catalized by VO(acac)2. Org. Lett., 2002, vol. 4, iss. 3, pp. 463-466.
DOI: https://doi.org/10.1021/ol017229j
[60] Anwar H.F., Skattebol L., Hansen T.V. Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines. Tetrahedron, 2007, vol. 63, iss. 40, pp. 9997-10002. DOI: https://doi.org/10.1016/j.tet.2007.07.064
[61] Locher C. Convenient preparation of some ^-substituted 1,2,3,4-tetrahydro-isoquinolines lacking electron-donating substituents. Synth. Commun., 2001, vol. 31, iss. 19, pp. 2895-2911. DOI: https://doi.org/10.1081/SCC-100105660
[62] Rivera A., Rios-Motta J., Navarro M.A. 7-(Imidazolidin-1-ylmethyl)quinolin-8-ol: an unexpected product from a Mannich-type reaction in basic medium. Heterocy-cles, 2006, vol. 68, no. 3, pp. 531-537. DOI: https://doi.org/10.3987/COM-05-10642
[63] Rivera A., Yorley D., González-Salas D., et al. X-ray and hydrogen-bonding properties of 1-((1H-benzotriazol-1-yl)methyl)naphthalene-2-ol. Molecules, 2009, vol. 14, iss 3, pp. 1234-1244. DOI: https://doi.org/10.3390/molecules14031234
[64] Rivera A., Maldonado M. Unexpected behavior of 6H,13H-5:12,7:14-dime-thanedibenzo[d,í][1,3,6,8]tetraazecine (DMDBTA) toward phenols. Tetrahedron Lett., 2006, vol. 47, iss. 42, pp. 7467-7471. DOI: https://doi.org/10.1016/j.tetlet.2006.08.045
[65] Rivera A., Rios-Motta J., Trujillo G.P., et al. Simple one-pot synthesis of new derivatives of the macrocyclic aminal 1,3,7,9,13,15,19,21-octaazapentacyclo-[19.3.1.13'7.19'13.115'19]octacosane (OAPO). Synth. Commun., 2013, vol. 43, iss. 6, pp. 791799. DOI: https://doi.org/10.1080/00397911.2011.609956
[66] Rivera A., Quevedo R. Solvent-free Mannich-type reaction of tetraazatricyclodo-decane (TATD) with phenols. Tetrahedron Lett., 2013, vol. 54, iss. 11, pp. 1416-1420. DOI: https://doi.org/10.1016/j.tetlet.2012.12.116
Slitikov P.V. — Dr. Sc. (Chem.), Professor, Department of Chemistry, Bauman Moscow State Technical University (2-ya Baumanskaya ul. 5, str. 1, Moscow, 105005 Russian Federation).
Evdokimenkova Yu.B. — Cand. Sc. (Chem.), Leading Researcher Department, Library of Natural Sciences, Russian Academy of Sciences (Znamenka ul. 11/11, Moscow, 119991 Russian Federation).
Please cite this article as:
Slitikov P.V., Evdokimenkova Yu.B. Aminomethylated hydroxinaphthalenes: synthesis and application. Herald of the Bauman Moscow State Technical University, Series Natural Sciences, 2021, no. 1 (94), pp. 126-143. DOI: https://doi.org/10.18698/1812-3368-2021-1-126-143
В Издательстве МГТУ им. Н.Э. Баумана вышла в свет монография авторов В.В. Кузенова, А.И. Лебо, И.Г. Лебо, С.В. Рыжкова
«Физико-математические модели и методы расчета воздействия мощных лазерных и плазменных импульсов на конденсированные и газовые среды»
Исследованы актуальные научные проблемы моделирования динамических процессов в экономических системах. Изложены основы моделирования динамики производственно-сбытовых и социально-психологических процессов взаимодействия экономических субъектов. Представлены разработанные авторами динамические модели, отражающие различные аспекты функционирования экономических систем в промышленности. Проанализированы прикладные аспекты использования инструментов системной динамики и агентного моделирования для исследования мультиагентного взаимодействия и проблем внедрения современных технологий цифрового производства.
По вопросам приобретения обращайтесь:
105005, Москва, 2-я Бауманская ул., д. 5, стр. 1
+7 (499) 263-60-45
press@bmstu.ru
Ьйрвг/ЛмпвШ.ргезв
