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AZ9RBAYCAN KIMYA JURNALI № 3 2018
ISSN 2522-1841 (Online) ISSN 0005-2531 (Print)
UDC 547.56.563.364
NORBORNENE-CONTAINING MANNICH BASES ON THE BASIS OF ALIPHATIC
AMINES
G.E.Hajiyeva1, E.H.Mammadbayli1, S.I.Ibrahimli2,1.A.Jafarov3
^u.Mamedaliyev Institute of Petrochemical Processes, NAS of Azerbaijan
2Ganja State University Azerbaijan State Pedagogical University
gulsum. mete@mail. ru
Received 15.12.2017
The novel norbornene-containing Mannich bases have been synthesized on the basis of norbornenyl-methanol, aliphatic amines and formaldehyde. The physico-chemical properties of obtained products have been determined. The structure and composition of synthesized compounds have been proved by the methods, of elemental analysis, IR spectroscopy, NMR1 H and 13C.
Keywords: dicyclopentadiene, norborneny¡methanol, secondary amines, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, Mannich bases.
Introduction
Functionally substituted organic compounds containing also heteroatoms, such as sulfur and nitrogen, are used as additives to improve the quality of oils and fuels, including those used in the form of effective biologically active substances, medical preparations, pesticides etc. [1, 2]. Depending on the nature and structure of the heteroatom, the biological activity and reactivity of these compounds varies.
Among the biologically active compounds of a number of norbornene, their amine-contai-ning derivatives are distinguished, the value of which is associated with the presence of two pharmacophore fragments - the nitrogen-containing group [3] and the carbon framework related to natural terpenes [4] - in their molecules. Since biologically active compounds, which combine several pharmacophore fragments, have more effective actions, the researchers try to expand the assortment of such compounds and study their physiological active properties [5].
The structure of bicyclo[2.2.1]heptane (norbornane) underlies many important natural compounds such as borneol, camphor etc. The norbornene fragment, like the norbornane and adamantane structures, form the basis of many amines that are drug substances. For amines with norbornan scaffolds, antiviral activity is characteristic [6].
The above-mentioned examples of the use
of nitrogen-containing compounds with the norbarnan fragment do not completely reflect the areas of their practical application, it stimulates research on elucidating the features of the course of the compounds involved in this reaction. It is important for researchers to synthesize new generations of such compounds on the basis of available raw materials and to find more advantageous methods for their production [7-9]. One of the convenient and effective methods for obtaining nitrogen-containing organic compounds is the Mannich reaction [10, 11].
Discussion of obtained results
In this paper properties of previously unknown aminomethoxy derivatives of norbornene obtained by the one-pot Mannich reaction of norbornenylmethanol (III) with aliphatic amines (V-IX) are considered. In the preparation of the starting norbornenylmethanol dicyclopentadiene, isolated from the C5 side fraction of the liquid pyrolysis products, is obtained from the EP-300 unit in Sumgayit city.
On the basis of dicyclopentadiene and al-lyl alcohol (II), norbornenylmethanol (III) was obtained. The reaction was carried out in an autoclave [12] at a reagent ratio of 1: 2.4 respectively, at a temperature of 170-180°C and a pressure of 4-5 atm, for 9 hours. At high temperature and pressure dicyclopentadiene mon-omerizes to cyclopentadiene, and as a result, the reaction proceeds according to scheme:
OH t,p
+ ^N/
II
The yield of the obtained alcohol (III) is
74%.
After synthesizing amino-methoxy derivatives of norbornenyl methanol (X-XTV), ami-nomethoxy derivatives of norbornenyl methanol (III), formaldehyde (IV) and secondary amines [diethylamine (V), dipropylamine (VI), dibutyla-mine (VII), dipentyl amine (Vm), dihexyl amine (IX)]. The yield of the target products is 43-71%. Reactions proceed according to the scheme:
or
in
+ ch2o + r2nh
iv v-ix
-h90
X-XIV
where R = C2H5 (V, X), C3H7 (VI, XI), C4H9 (VII, XII), CsHn (VIII, XIII), C6Hi3 (IX, XIV).
It can be assumed that an N-oxymethyl derivative is formed intermediately:
0
11 An
h
v-ix
oh I +
-h2c-nr2
0
I +
h2c-nr2-
h
H
iv
A 4
ch9oh
h,c—nr9
-H
iii
h9c=nr9
o nr9
x-xiv
After the initial attack of the carbon atom of the carbonyl group by the electron pair of the nitrogen atom, which is not separated by a pair of electrons, protonation and splitting of water follows, resulting in the formation of a cation. Attacking the positively charged carbon atom of
said cation with a carbanion formed from 5-(norborn-2-enyl)methanol (III) leads to the formation of Mannich bases (X-XIV).
The reactions were carried out in a solution of benzene at 78-80°C for 4-5 h with an equimolar ratio of the reagents. Compounds (X-XIV) are liquids with a characteristic odor, insoluble in water, readily soluble in organic solvents (ethanol, acetone, benzene, CCI4, CHCI3 etc.). The composition and structure of the obtained compounds (III, X-XIV) were confirmed by elemental analysis data, IR spectroscopy, lH NMR and 13C. In the IR spectra of 5-(norborn-2-enyl)methanol (III), a broad absorption band is observed in the 3500 cnT1 region characteristic of the hydroxyl group [13], and in the IR spectra of the aminomethoxy derivatives norborn-5-ene (X-XIV) this absorption band is absent. Absorption bands in the 1288-1100 cirf1 field are characteristic for stretching vibrations of the C-N bonds (X-XIV). In addition, absorption bands were observed in the regions 2857-2853 cirf1, which are characteristic for the C-H (vc-h) bond of the CH3 and CH2 groups respectively. Valentine vibrations of the C-0 bond (vc-o) appear in the field of 1100-1048 cm"1 in the form of an intense absorption band. The lH and 13C NMR spectra of synthesized compounds confirm their indicated structure. The IR spectrum of compound (XII), NMR *H spectrum of compound
13
(X) and C spectrum of compound (XI) are cited in Figure 1-3.
Experimental
The IR spectra of synthesized compounds were taken with the apparatus "SPEKTRUM BX" and "BRUKER" from ALPHA IR FURYE (Germany) in the range 4000-400 cm4. The 'h and 13C NMR spectra were recorded on a BRUKER AM-300 spectrometer, at a frequency of 300 MHz in a CeD6 solvent, the internal standard was hexamethyldisiloxane.
The purity of the reaction products was determined by boiling point, elemental analysis and gas-liquid chromatography.
Elemental analysis was carried out using a "CARLOERBA" device - EA 1108.
8 0 10 ц г п о"" " N
1__А
—кС —н (___
И-11 1 I ' 'Ч'"'!"' ' Т"""-
7 5 7.0 5.5 6.0 5.» £.0 4,5 4,0 3,8 3.0 2.6 2.0 1.5 1.0 0.5 рр<п
г
Fig. 1. 'Н ЫМЯ врейгат о! 5ЧН,М-01е%1а1гапотеШохутеЛу1)Ь1сус1о[2.2.1]Ьер1-2-епе (X).
220 200 180 160 140 130 1 00 М 60 *0 20 ррт
2. |3С ЫМЯ вресЛгит оГ 5-(>[,М-<11ршру1а1шпоше1Ьохуте111у1)Ьюус1о[2.2.1]Ьер1-2-епе (XI).
8
з -
я
2500 2 ООО
\Vave питЬег, ст"1
Fig. 3.ГО. вресйито!' 5^,Ы-БШи1у1ат1потсИюхутеШу1)Ь1сус1о|2.2.1 |Ьер1-2-епе (XII).
GLC analysis was performed on a chro-matograph LXM-8 MD, steel column (300x3 mm) with 5% PEGS (polyethylene glycol succinate) on Dichrome P, carrier gas - helium (40 cm /min), detector cathrometer, column temperature
150°C, evaporator - 230°C.Refractive index (n f ) - on a refractometer of the brand "ABBEMAT" 350/500, density (pf ) - on the instrument "DMA" 4500 M.
The starting allyl alcohol was reactive. Before use, it was dried over MgSC>4 and distilled. On the basis of allyl alcohol and cyclo-pentadiene 5-(norborn-2-enyl)methanol (III) was prepared by the procedure of [12], which is the starting reagent in the further synthesis of norbornenyl-containing Mannich bases.
Diethylamine (V), dipropylamine (VI), dibutylamine (VII), dipentylamine (VIII) and dihexylamine (IX) there were used reactive. Before use, all five aliphatic secondary amines were distilled and determined their physico-chemical constants, which coincide with the literature data.
Ammoniac water, which is a medical preparation, was used as a 10% solution. Benzene was used as the solvent, which was purified and dried by the known method [14].
Paraformaldehyde is a product of formaldehyde polymerization, consisting of 8-100 monomers. When heated, it is depolymerized to formaldehyde. It was used as a reactive powder.
5-(Norborn-2-enyl)methanol (III) was prepared in an autoclave by the procedure of [12] for 9 hours at a temperature of 170-180°C, a pressure of 4-5 atm with a ratio of dicyclo-pentadiene and allylic alcohol (II) of 1:2.4 respectively. The yield of the desired product was 74%. The boiling point is 82-836C (10 mm
Hg), n2° 1.4970, pf 1.027 g/cm3. IR spectrum, v, cm"1: 3500 (OH), 2880-2830 (C-H, CH2), 1200-1100 (C-N). NMR ^ 5, ppm: 0.45 d.d (1H, C6Hexo, ./=4.1 Hz), 1.19 t (1H, C7Ha, ./=7.9 Hz), 1.44 t (1H, C6Hendo, J= 4.1 Hz), 1.68 m (1H, C7H„ J=1.9 Hz), 2.86 q (1H, C5H), 3.21-3.36 t (1H, C4H), 3.36-3.46 d.d (2H, C8H2), 3.46 t (H, C^H), 3.92 bp.s iH, OH), 6.00-6.08 m (2H, C2H, C3H). NMR 13C, 5, ppm: 28.83
(C6), 41.76 (C5), 42.26 (C1), 43.60 (C4), 49.41 (C7), 65.76 (C8), 132.32 (C3), 137.78 (Cf).
Aminomethoxy derivatives of norborn-5-ene (X-XIV). General methodology. To 0.2
moles of paraform (IV) diluted in 20 ml of benzene, 0.1 mole of norbornenyl methanol (III) diluted in 20 ml of benzene was added dropwise with stirring. Then, while stirring, a solution of 0.1 moles of secondary amine (V-IX) in 20 ml of benzene was added dropwise. Stirring was continued at 78-80°C for 4-5 hours. After cooling, the mixture was treated with an ammonia solution (10%>). Washed with distilled water until neutral and dried over MgSOzj. The benzene was distilled off, the residue was distilled in a vacuum.
5-(N,N-Diethylaminomethoxymethyl)bi-cyclo[2.2.1]hept-2-ene (X) was prepared from 12.4 g (0.1 mole) of norbornenylmethanol (III), 6 g (0.2 mole) of paraform (IV) and 14.6 g (0.2 mole) of diethylamine (V). Yield - 10.6 g (51%), b.p. - 102-104°C (4 mm Hg), n2° -1.4672, pf - 0.9395 g/cm3. IR spectrum, v, cm"1: 3057.66, 978.83, 932.86, 816.75 (C-H, CH=CH); 2961.78, 2858.75, 1460.29, 1359.48 (5 C-H, CH, CH2, CH3); 1629.96 (C=C); 1215.33 (C-N); 1057.02 (C-O-C); 715.65 (C-
H, CH2). NMR 1H, 5, ppm: 1.042 t (6H, C13'15H3, J= 7.5 Hz), 1.265-1.373 m (2H, C6H2),
I.787 d.d.d (2H, C7H2; J=2.2, 2.1, 1.2 Hz), 2.685-2.927 m (3H, CU5H), 3.295-3.424 m (4H, C12'14H2N), 3.424 d (2H, C8H20, J= 6.8 Hz), 4.170 s (2H, C10H2), 5.934-5.951 m (1H, C2H=), 6.105-6.116 m (1H, C3H=). NMR 13C, 5, ppm: 12.85 (C13'15), 29.01 (C6), 38.87 (C5), 42.06 (C1), 43.86 (C4), 45.11 (C7), 49.03 (C12'14), 71.07 (C8), 84.14 (C10), 132.36 (C2), 136.64 (C3). Found, %: C 74.06, H 10.86, N 6.61. Ci3H23NO. Calculated, %: C 74.64, H 11.00, N6.70.
5-(N,N-dipropylaminomethoxymethyl)-bicyclo[2.2.1]hept-2-ene (XI) was prepared from 10 g (0.08 mole) of norbornenylmethanol (HI), 5 g (0.16 mole) of paraform (IV) and 8 g (0.08 mole) of dipropylamine (VI). Yield - 8.05 g (43%), b.p. -119-122°C (4 mm Hg), n2° - 1.4670, pf -0.9228 g/cm3. IR spectrum, v, cm"1: 3059.09,
54
G.E.HAJIYEVA et al.
983.40, 962.53, 938.20, 903.37 37 (S C-H, CH=CH); 2957.87, 2933.86, 2868.20, 1463.87, 1364.11, 1343.50 (C-H, CH, CH2, CH3); 1685.15 (C=C); 1202.44 (C-N); 1091.97, 1068.70, 1048.05 (C-O-C); 717.83 (mathematical oscillation C-H, CH2). NMR 1H, ô, ppm: 0.885-0.911 t (6H, С14Д7Н3), 1.268-1.465 m (7H, C1316H2, C5H, C6H2), 1.792 m (2H, C7H2), 2.575 d.d (1H, C*H, J=0.1, 1.2 Hz), 2.773 d.d (1H, C4H J=0.1, 1.2 Hz), 2.930-3.115 m (6H, С8Д2Д5Н2), 4.078 s (2H, C10H2), 5.942-6.116 m (2H, C2'3H=). NMR 13C, ô, ppm: 11.30 (C14'17), 21.16 (C13'16), 29.01 (C6), 38.88 (C5), 42.06 (C1), 43.87 (C4), 49.04 (C7), 53.73 (Cù'15), 71.11 (C8), 85.23 (C10), 132.37 (C2), 136.63 (C3). Found, %: С 75.22, H 11.96, N 5.17. Ci5H27NO. Calculated, %: С 75.95, H 11.39, N 5.91.
5-(N,N-Dibutylaminomethoxymethyl)bi-cyclo[2.2.1]hept-2-ene (XII) was prepared from 12.4 g (0.1 mole) of norbornenylmethanol (III), 6 g (0.2 mole) of paraform (IV) and 12.9 g (0.1 mole) of dibutylamine (VII). Yield - 13 g (49%),
(0.1 mole) of dipentylamine (VIII). Yield - 21 g
(71%), b.p. - 185UC (13 mm Hg), n2° - 1.4680,
b.p. - 135 C (2 mm Hg), n^ - 1.4660, pf-0.9100 g/cm3. IR spectrum, v, cm4: 3059.11, 984.47, 960.39, 933.86, 904.21 (C-H, CH=CH); 2955.89, 2931.32, 2862.49, 2803.96, 1459.26, 1364.32, 1343.73 (C-H, CH2, CH3); 1685.27 (C=C); 1272.85, 1251.53, 1190.57 (C-O-C); 1070.08, 1048.83 (5 C-N); 717.92 (mathematical oscillation C-H, CH2). NMR 1H, 5, ppm: 0.922 t (6H, C15'19H3, J=1.1 Hz), 1.347-1.505 m (7H, C6'14'18H2, C5H), 1.791 d.d.d (2H, C7H2, J=2.3, 2.1, 1.2 Hz), 2.474 d.d (1H, C1^ J=0.1, 1.2 Hz), 2.636 d.d (1H, C4H, J=0.1, 1.2 Hz), 2.772-2.930 m (4H, C13'17H2), 3.001-3.117 m (6H, C8'12'16H2), 4.076 s (1H, C10H), 4.094 s (1H, C10H), 5.936-5.945 m (1H, C2H=), 6.108-6.118 m (1H, C3H=). NMR 13C, 5, ppm: 13.56 (C15'19), 20.31 (C14'18), 29.01 (C6), 30.27 (C13'17), 38.88 (C5), 42.07 (C1), 43.87 (C4), 49.05 (C7), 51.41 (C12'16), 71.12 (C8), 85.11 (C10), 132.37 (C2), 136.64 (C3). Found, %: C 76.60, H 10.64, N 5.96. C17H31NO. Calculated, %: C 75.47, H 10.93, N5.22.
5-(N,N-Dipentylaminomethoxymethyl)-bicyclo[2.2.1]hept-2-ene (XIII) was prepared from 12.4 g (0.1 mole) of norbornenylmethanol (III), 6 g (0.2 mole) of paraform (IV) and 15.7 g
pf - 0.9057 g/cmJ.
IR spectrum, v, cm4: 3059.14, 984.35, 962.72, 936.78, 903.88 (C-H, CH=CH); 2956.51, 2931.00, 2862.51, 1462.17, 1376.94, 1343.69 (C-H, CH2, CH3); 1686.00 (C=C); 1252.93, 1224.92, 1192.25 (C-O-C); 1069.86, 1050.78 (5 C-N); 718.01 (mathematical oscillation C-H, CH2). NMR 1H, Ô, ppm: 0.81-0.95 t (6H, C16'21H3, J= 13 Hz), 1.00-1.60 m (12H, C13"15'18"20H2), 1.33-1.52 m (5H, C6H2, C14'5H), 1.79 d.d.d (2H, C7H2, J=2.2, 2.1, 1.2 Hz), 3.0-3.34 m (6H, C8H20, C12'17H2N), 4.08 s (1H, OC10H2N), 4.09 s (1H, OC10H2N), 5.94-5.95 m (1H, C2H=), 6.11-6.12 m (1H, C3H=). NMR 13C, Ô, ppm: 10.89 (C16), 13.63 (C21), 17.16 (C15), 22.47 (C20), 27.24 (C14), 27.76 (C19), 33.16 (C13), 38.88 (C18), 42.06 (C6), 43.87 (C5), 49.05 (C1), 51.69 (C4), 52.27 (C7), 58.65 (C17),
59.55 (C12), 71.23 (C6), 85.51 (C1U), 132.37 (C2), 136.65 (C3). Found, %: C 77.36, H 12.27, N 4.03. C19H35NO. Calculated, %: C 77.82, H 11.95, N4.78.
5-(N,N-Dihexylaminomethoxymethyl)bi-cyclo[2.2.1]hept-2-ene (XIV) was prepared from 12.4 g (0.1 mole) of norbornenylmethanol (HI), 6 g (0.2 mole) of paraform (IV) and 15.7 g (0.1 mole) of dihexylamine (IX). Yield - 20.4 g (64%), b.p. - 192-194°C (6 mm Hg), n2° -1.4645, pf -0.8854 g/cm3.
Юч
IR spectrum, v, cm4: 3058.20, 987.49, 839.70 (C-H, CH=CH); 2927.88, 2857.86, 1459.83, 1361.95 (C-H, CH2, CH3); 1635.05 (C=C); 1221.39, 1172.05, 1063.83 (Ô C-N); 1172.05 (C-O-C); 717.75 (mathematical oscil-
lation C-H, CH2). NMR 1H, 5, ppm: 0.91 t (6H, C17'23H3, ,7=7.1 Hz), 1.32-1.48 m (16H, C13"1619" 22H2), 1.79 d.d.d (2H, C7H2, J=2.2, 2.1, 1.2 Hz), 2.47 d.d (1H, C'H, J=0.1, 1.2 Hz), 2.63 d.d (1H, c'll. ./ 0.1. 1.2 Hz), 3.0-3.12 m (611. C81218H2), 4.08 s (1H, C10H2), 4.09 s (1H, C10H2), 5.94-6.11 m (2H, C23H). NMR 13C, 6, ppm: 13.57 (C17"23), 22.56 (C16"22), 26.97 (C15-21), 27.21 (C14-20), 28.03 (C13"19), 31.75 (C6), 38.89 (C5), 42.07 (C1), 43.88 (C4), 49.04 (C7), 51.71 (C12), 51.76 (C18), 71.12 (C8), 85.16 (C10), 132.37 (C2), 136.63 (C3). Found, %: C 77.98, H 12.41, N 4.04. C2iH39NO. Calculated, %: C 78.50, H 12.15, N4.36.
Conclusion
Thus, previously not known norbornene-containing bases of Mannich based on norborne-nylmethanol and aliphatic secondary amines and formaldehyde have been synthesized. Optimum conditions for obtaining the target products are found. The reaction was carried out at an equimolar ratio of the initial reagents at a temperature of 78-80°C in the presence of benzene for 4-5 hours, while the yield was 43-71%. Obtained liquid compounds with a characteristic odor, insoluble in water, readily soluble in organic solvents (ethanol, acetone, benzene, CCU, CHC13 etc.). The physicochemical constants of the synthesized compounds are determined. The structure of the compounds obtained is confirmed by the methods of elemental analysis, IR spectroscopy, NMR lFI and 13C,
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ALiFATIK AMINLOR 9SASINDA NORBORNEN T9RKIBLi MANNiX OSASLARL
G.9.Haciyeva, E. H. IVIom mod hoy I i, S.Librahimli, LA.Cafarov
Norbomenilmetanol, alifatik aminlor vo formaldehid asasmda yeni norbornen torkibli Mannix osaslan sintez cdilmisdir. Ahnan maddolorin fiziki-kimyavi xassolori oyronilniisdir Sintez olunmus maddoloiin lorkib vo quail us u element analizi, lQ, 'H \o 'C NMR spektroskopiya tisullan 1I0 losdiq edilmisdir.
Agar sozbr: ditsiklopentadien, norbornenilmetanol, ikili aminlar, dietilamin, dipropilamin, dibutilamin, dipentilamin, diheksilamin, Mannix asaslari.
56
О.Е.НАЛУЕУА с* а1.
НОРБОРНЕНСОДЕРЖАЩИЕ ОСНОВАНИЯ МАНННХА НА ОСНОВЕ АЛИФАТИЧЕСКИХ АМИНОВ
Г.Э.Гаджиева, Э.Г.Мамедбейли, С.И.Ибрагимли, И.А.Джафаров
На основе норборненилметанола, алифатических аминов и формальдегида синтезированы новые норборненсо-держащие основания Манниха. Определены физико-химические характеристики целевых продуктов. Состав и строение синтезированных соединений подтверждены методами элементного анализа, ИК-спектроскопии, ЯМР :Н и 13С.
Ключевые слова: дициклопентадиен, норборненилметанол, вторичные амины, диэтиламин, дипропиламин, дибутиламин, дипентиламин, дигексиламин, основания Манниха.
