CC BY
10DOI: 10.6060/ivkkt.20186108.5817
УДК: 547.304.2 + 547.853
СОЛИ ТРОПИЛИЯ И ТРИТИЛИЯ В РЕАКЦИЯХ С 2-АМИНО-4,6-ДИЗАМЕЩЕННЫМИ ПИРИМИДИНАМИ
Л.П. Юнникова, В.В. Эсенбаева, Е.В. Шкляева
Лидия Петровна Юнникова, Виктория Викторовна Эсенбаева
Кафедра общей химии, Пермский государственный аграрно-технологический университет им. академика Д.Н. Прянишникова, ул. Петропавловская, 23, Пермь, Российская Федерация, 614990 Е-mail: yunnikova@yahoo.com, Cherniialmaz@mail.ru
Елена Викторовна Шкляева
Кафедра органической химии, Пермский государственный национальный исследовательский университет, ул. Букирева, 15, Пермь, Российская Федерация, 614990 Е-mail: Shkelvik@gmail.com
Взаимодействие тетрафторборатов тропилия или тритилия с 2-амино-4,6-диметилпиримидином в среде этанола при комнатной температуре приводит, соответственно, к 4,6-диметил-2-(М-циклогепта-2',4',6'-триен-1'-иламино)пиримидину и 4,6-диметил-2-(Ы-тритиламино)пиримидину, что связано с подвижностью протонов аминогруппы вследствие амино-иминной таутомерии. Результат взаимодействия тетрафтор-бората тропилия с 2-амино-4,6-дигидроксипиримидином в аналогичных условиях зависит от соотношения исходных реагентов. Установлено три направления реакции: при использовании соотношения 1 : 1,5 образуется 4,6-дигидрокси-2-(М-циклогепта-2',4',6'-триен-1'-иламино)пиримидин, содержащий только один тропилиевый фрагмент у атома азота аминогруппы; введение в реакцию двойного избытка соли в один прием приводит к 4,6-дигидрокси-2-(М,М-дициклогепта-2',4',6'-триен-1'-ил)аминопиримидину, содержащему два тропилиевых фрагмента у атома азота аминогруппы, образование этого амина можно объяснить высокой подвижностью атомов водорода в аминогруппе вследствие амино-иминной таутомерии и кинетического контроля процесса; последовательное введение соли с интервалом 1,5 ч приводит к 2-(М-циклогепта-2',6',4'-триен-1'-иламино)-3-(циклогепта-2',4',6'-триен-1'-ил)-6-гидроксипиримидин-4(3Н)-ону, в котором замещены атомы водорода у экзоциклического и эндоциклического атомов азота гетероцикла. Третье направление реакции, связанное с добавлением второго эквивалента соли с интервалом 1,5 ч, способствует повышению концентрации таутомера, возникающего вследствие лактам-лактимной таутомерии. Структура всех полученных соединений подтверждена данными 1Н ЯМР спектроскопии и масс-спектрометрии, а также методом рентгеноструктурного анализа.
Ключевые слова: соли тропилия, тритилия, 2-амино-4,6-диметилпиримидин, 2-амино-4,6-ди-гидроксипиримидин
TROPYLIUM AND TRITYLIUM SALTS IN REACTIONS WITH 2-AMINO-4,6-DISUBSTITUTED PYRIMIDINES
L.P. Yunnikova, V.V. Esenbaeva, E.V. Shklyaeva
Lidia Yunnikova, Victoria V. Esenbaeva
Department of chemistry, Perm state agricultural and technological University. academician D.N. Pryanishni-kov, Petropavlovskaya str., 23, Perm, Russian Federation, 614990 E-mail: yunnikova@yahoo.com (author), Cherniialmaz@mail.ru
Elena V. Shklyaeva
Department of organic chemistry, Perm state national research University, Bukireva St., 15, Perm, Russian
Federation, 614990
E-mail: Shkelvik@gmail.com
Interaction of tropylium or tritylium tetrafluoroborate with 2-amino-4,6-dimethyl-pyrimidine in an ethanol medium at room temperature was found out to result in 4,6-dimethyl-2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)pyrimidine and 4,6-dimethyl-2-(N-tritylamino)pyrimidine. Interaction between tropylium tetrafluoroborate and 2-amino-4,6-dihydroxypyrimidine under similar conditions is dependent on the ratio of starting reagents. Three reaction routes have been ascertained: with the ratio 1 : 1.5, 4,6-dihydroxy-2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)-pyrimidine containing only one tropylium moiety at the nitrogen atom of amino group is formed; addition of a double excess of the salt at one go leads to 4,6-dihydroxy-2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)aminopyrimidine containing two tropylium moieties at the nitrogen atom of amino group, formation of amine can be explained by a high mobility of hydrogen atoms in amino group because of the amino-imine tautomerism and kinetic control of the process; sequential addition (every 1.5 h) of the salt leads to formation of 2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)-3-(cyclohepta-2',4',6'-triene-1'-il)-6-hydroxypyrimidin-4(3H)one in which the hydrogen atoms at exocyclic and endocyclic nitrogen atoms of the heterocycle are substituted. The reaction route, characterized by sequential addition (every 1.5 h) of the salt, contributes to an increase in concentration of the tautomer because of the lactam-lactim tautomerism resulting in amine. The structure of all the compounds so produced is confirmed by the findings of 1H NMR spectroscopy, mass-spectrometry, andXRD analysis.
Keywords: tropylium/tritylium salts, 2-amino-4,6-dimethylpyrimidine, 2-amino-4,6-dihydroxypyrimidine Для цитирования:
Юнникова Л.П., Эсенбаева В.В., Шкляева Е.В. Соли тропилия и тритилия в реакциях С 2-амино-4,6-дизамещен-ными пиримидинами. Изв. вузов. Химия и хим. технология. 2018. Т. 61. Вып. 8. С. 47-52 For citation:
Yunnikova L.P., Esenbaeva V.V., Shklyaeva E.V. Tropylium and tritylium salts in reactions with 2-amino-4,6-disub-stituted pyrimidines. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2018. V. 61. N 8. P. 47-52
Tropylium/tritylium salts have been used for either C-tropylization or N-tritylization of aromatic [15] or heterocyclic [6] amines. Besides, stable and reactive tropylium salts [7] have been used as hydride-ion acceptors. Oxidative functionalization of tetrahydroi-soquinolines at C1 position with use of tropylium tetrafluoroborate appears to be an example of interest.
2-Amino-4,6-dimethylpyrimidin and 2-amino-4,6-dihydroxypyrimidine 1a, b belong to a group of known pharmacophores which are of interest for synthesis of new compounds with potential biological activity [8-14]. Reactivity of these compounds can be attributed to mobility of protons of the NH2 and OH groups because of appearance of the amino-imine (for 1a, 1b) and lactam-lactim tautomerism (for 1b) [15-19].
This work aims at investigation of a possibility of N-tropylization and N-tritylization for compounds 1a and 1b.
Interaction of tropylium 2 and tritylium 3 tetrafluoroborate with 2-amino-4,6-dimethylpyrimidine 1a in an ethanol medium at room temperature was found out to result in 4,6-dimethyl-2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)pyrimidine 4 and 4,6-dimethyl-2-(N-tritylamino)pyrimidine 5, respectively.
The result of interaction between tropylium tet-rafluoroborate 2 and 2-amino-4,6-dihydroxypyri-midine 1b under similar conditions is dependent on the ratio of starting reagents. Three reaction routes have been ascertained: (1) with the ratio 1 : 1.5, 4,6-dihydroxy-2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)-pyrimidine containing only one tropylium moiety at the nitrogen atom of amino group is formed; (2) addition of a double excess of the salt 2 at one go leads to formation of 4,6-dihydroxy-2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)-aminopyrimidine containing two tropylium moieties at the nitrogen atom of amino group; (3) sequential addition (every 1.5 h) of the salt 2 leads to formation of 2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)-3-(cyclohepta-2', 4',6'-triene-1'-il)-6-hydroxy-pyrimidin-4(3H)one 8 in which the hydrogen atoms at exocyclic and endocyclic nitrogen atoms of the heterocycle are substituted.
In the reaction route (2), formation of amine 7 can be explained by a high mobility of hydrogen atoms in amino group 1b because of the amino-imine tautomerism and kinetic control of the process. The reaction route (3), characterized by sequential addition (every 1.5 h) of the salt 2, contributes to an increase in concentration of the tautomer A because of the lactam-lactim tautomerism resulting in amine 8. The latter result is confirmed by formation of amine 8 obtained by interaction between amine 6 and salt 2.
но но
BF/
HO
1:1
HO
The structure of all the compounds so produced is confirmed by the findings of :H NMR spec-troscopy, mass-spectrometry, and XRD analysis for substances 4 and 5 (Figure).
According to the data of X-ray diffraction analysis, the compound 4 crystallizes in a space cen-trosymmetric group of a monoclinic crystal system. The bonds length and bond angles in a molecule are close to the standard values of corresponding atoms. Pyrimidine cycle is plane within 0.01 Á. The cyclo-heptatriene cycle is in a boat-like conformation. Atoms C11, C10 and C7 are removed from a plane C9C8C12C13 at 0.51, 0.50 and 0.7Á respectively. The dihedral angle between C9C8C12C13 plane and the plane of pyrimidine cycle is 72.8 In a crystal, the molecules are connected by intermolecular hydrogen bonding N3-H^-N2, d(N3-N2) 3.095(2) Á, d(N3- H34) 0.843(2) Á, d(H34- N2) 2.260(2) Á. The molecules of a compound form dimers by intermolecular hydrogen bonding.
HO b •
5
Fig. The structure of 2-(N-cyclohepta-2',4',6'-triene-1-il)amino-4,6-dimethylpyrimidine 4 and the structure of 4,6-dimethyl-2-(N-
tritylamino)pyrimidine 5. Рис. Структура 2-(Ы-циклогепта-2,4,6-триен-1-ил)амино-4,6-диметилпиримидина 4 и структура 4,6-диметил-2-(№ тритиламино)пиримидина 5.
The compound 5 crystallizes in a space cen-trosymmetric group of a monoclinic crystal system. Pyrimidine cycle is plane within 0.025 Â. Angle of C-N-C stands at 128.5(2) °.
4
The CIF files containing complete information on the structures under scrutiny was deposited with the CCDC and registered as Nr. 1850688 for compound 4, and Nr. 1850689 for compound 5. The file may freely be retrieved upon request at www.ccdc.cam.ac.uk/da-ta_request/cif.
EXPERIMENTAL PART
The 1H NMR spectra were registered on the Mercury 400 device (400 MHz), with HMDS as internal standard. The mass spectra were registered on the maXis Impact HD mass spectrometer (Bruker, Germany). The Xcalibur R diffractometer was used to measure parameters of the elemental cell and of back-scattered intensity. An empirical absorption correction was applied to the findings using the SCALE3 ABSPACK scaling algorithm [20]. The structure was determined by the direct method and corrected by the full matrix OLS method with use of the SHELX-2013 software package [21].
2-(N-cyclohepta-2',4',6'-triene-1-il)amino-4,6-dimethylpyrimidine 4. A 0.36 g portion (2 mmol) of salt 2 was added at one go to 0.49 g (4 mmol) of amine 1a dissolved in 5 ml of EtOH. The reaction mass was stirred for 3 h at room temperature. After removal of the solvent, 10% solution of NH3 was added to adjust the pH value to 7-8. Precipitate of white color. Yield: 0.31 g (72.8%); m.p. 115-116 °C (hexane). >H NMR (CDCh), 5, ppm: 2.31 s (6H, 2CH3), 4.47-4.54 m (1H, CrH), 5.57 ddt (2H, J 9.3 Hz, J 5.9 Hz, J 0.8 Hz, C2H, C7H), 6.07 s (1H, NH), 6.27 dddd (2H, J9.2 Hz, J3.8 Hz, J2.7 Hz, J0.9 Hz, C3'H, C6H), 6.33 s (1H, CH), 6.71 ddt (2H, J 3.5 Hz, J 2.7 Hz, J 0.8 Hz, C4H, C5H). Found: 214.1342 [M+ +H]+ C13H15N3. Calculated for [C^H^f 214.1339.
The crystals of compound 4 are monoclinic, steric group I 2/a, a = 11.617(3), b = 10.532(3), c = 19.530(5) Ä, ß = 94.55(3) V = 2382.0(11) Ä3, d calculated = 1.189, ^ = 0.073 MM-1, C13H15N3, Z = 8. Finite correction parameters: R1 = 0.0557, wR2 = 0.1381 [for 1968 reflections with I> 2o(Z)], R1 = 0.0825, wRi = 0.1544 (for all 2810 independent reflections, Rmt = 0.0259), S = 1.033.
4,6-Dimethyl-2-(N-tritylamino)pyrimidine 5.
A 0.20 g portion (0.60 mmol) of salt 3 was added at one go to 0.09 g (0.73 mmol) of amine 1a dissolved in 6 ml of CH2Cl2. The reaction mass was stirred for 2 h at room temperature. After removal of the solvent, 10% solution of NH3 was added to adjust the pH value to 7-8. Precipitate of white color. Yield: 0.15 g (68%); m.p. 144-146 °C (hexane). NMR (CDCh), 5, ppm: 2.05 s (6H, 2CH3), 2.80 s (1H, NH), 6.20 s (1H, C5H), 7.17-7.36 m (15H, 3Ph). Found: 366.1959 [M+HT C25H23N3. Calculated for [C25H23N3]+ 366.1965.
The crystals of compound 5 are monoclinic, steric group P2:/n, at 295.0(2) K: a 13.9281(36), b 9.0686(23), c 16.3790(41) A; p 103.665(26) °; V 2010.24(131) A3; Z 4; d calculated 1.21 g/cm3; ^(000) 776; ^ 0.072 mm-1. Finite divergence factors: R1 0.0579, wR2 0.1373 for reflections with I > 2o(I), R1 0.1132, wR2 0.1621 (for all reflections), S 1.002. Completeness of collected findings for 9 < 26.00 0 equals 99.8%. Maximal and minimal values of residual electron density peaks equal 0.172 and -0.222 e/A3, respectively.
4,6-Dihydroxy-2-(N-cyclohepta-2',4',6'-triene-1-il)aminopyrimidine 6. A 0.065 g portion (0.37 mmol) of salt 2 was added to 0.07 g (0.55 mmol) of amine 1b suspended in 10 ml of ethanol. The reaction mass was stirred for 2 h at room temperature; at this point, the initially rosy solution turned light-yellow. After that, 10% solution of NH3 was added to the reaction mass to adjust the pH value to 7-8. The white crystals were filtered off and rinsed with ethanol and ether. Yield 0.065 g (82%), m.p. 215 °C (with decomposition). NMR (DMSO-d6), 5, ppm: 2.67 t (1H, J 5.5 Hz, CrH), 5.26 dd (2H, J 9.1 Hz, J 5.5 Hz, C2H C7H), 6.02 dd (2H, J 9.2 Hz, J 2.0 Hz, C3H C6H), 6.42-6.70 m (4H, C4H C5H+NH, C5H), 10.41 s (2H, 2OH). Found: 218.0924 [M+H]+ C11H11N3O2. Calculated for [CnH:2N3O2]+ 218.0924.
4,6-Dihydroxy-2-(N,N-dicyclohepta-2',4',6'-triene-1'-il)aminopyrimidine 7. A 0.063 g portion (0.5 mmol) of amine 1b was added to 0.17 g (1 mmol) of salt 2 suspended in 20 ml of ethanol. The reaction mass was stirred for 4 h at room temperature. After 3 h stirring, the initially bright-yellow solution turned orange. The sediment was filtered and rinsed with water. With additional 5 ml of water added, the precipitate was neutralized dropwise with 10% solution of NH3 to attain pH 7, light-yellow crystals were filtered off and rinsed with ethanol and ether. Yield 0.08 g (75%), m.p. 180 °C (with decomposition). >H NMR (DMSO-d6), 5, ppm: 2.37 tt (2H, J5.9 Hz, J 1.4 Hz ), 5.35-5.12 m (4H), 6.16 dddd (4H , J 9.1 Hz, J 4.0 Hz, J 2.7 Hz, J 1.3 Hz) 6.67 dd (4H, J 3.6 Hz, J 2.5 Hz), 6.78 s (1H), 8.25 s (1H), 11.11 s (1H). Found: 308.1393 [M + H]+ C18H17N3O2. Calculated for [C1sH18N3O2]+ 308.1394.
2-(N-cyclohepta-2',4',6'-triene-1'-ilamino)-3-(cyclohepta-2',4',6'-triene-1'-il)-6-hydroxypyri-midin-4(3H)one 8. A 0.180 g portion (1 mmol) of salt 2 was added to 0.127 g (1 mmol) of amine 1b suspended in 20 ml of ethanol while stirred. 1.5 Hour later, a second 0.180 g portion (1 mmol) of salt 2 was added to the suspension colored bright-yellow, whereupon the reaction mass was stirred for 2 h at
Л. П. Юнникова, В.В. Эсенбаева, Е.В. Шкляева
room temperature. The yellow precipitate was treated with 10% solution of NH3 to attain pH 7, separated and rinsed with hexane and ether. Yield 0.17 g (55%), m.p. 190 °С (with decomposition). 1H NMR (DMSO-de), 5, ppm: 2.38 t (1Н, J5.9 Hz, СГН), 2.69 tt (1Н, J 5.4 Hz, J 1.5 Hz, СГН), 5.24-5.33 m (4Н, С2Н, С7Н, С2'Н, С7'Н), 6.0 dddd (2Н, J 8.8 Hz, J 3.8 Hz, J 2.6 Hz, J 1.6 Hz, С3Н, С6Н), 6.15 dddd (2Н, J 8.8 Hz, J 3.8 Hz, J 2.6 Hz, J 1.6 Hz, С3Н, С6Н), 6.56 t (2Н, J 3.1 Hz, С4Н, С5Н), 6.66 t (2Н, J 3.0 Hz, С4Н, С5Н), 8.20 m (3Н, NH, С5Н, ОН). Found: 308.1395 [М + H]+ C18H17N3O2. Calculated for [C18H18N3O2]+ 308.1394.
ЛИТЕРАТУРА
1. Yunnikova L.P. Hydroalkylation of imines by cyclohepta-
1.3.5-trien. Mendeleev Comm. 1996. N 3. P. 25-26.
2. Yunnikova L.P., Akentieva T.A., Makhova T.V. One-pot three synthesis of N-arylmethyl-4-(7-cyclohepta-1.3.5-trienyl)anilines. Int. J. Organic Chem. 2013. V. 3. N 2. P. 148-150. DOI: 10.4236/ijoc.2013.32017.
3. Юнникова Л.П., Акентьева Т.А., Эсенбаева В.В. Тропилирование ариламинов и антимикробная активность 4-(7-циклогепта-1,3,5-триенил)-N-(1 -циклогепта-
2.4.6-триенил)анилина Тропилирование ариламинов и антимикробная активность 4-(7-циклогепта-1,3,5-триенил)-N-(1-циклогепта-2,4,6-триенил)анилина. Хим.-фарм. ж. 2015. Т.49. № 4. С. 33-35.
4. Takahashi K., Takenaka S., Nozoe T. Cyclic cross-conjugated hydrocarbons having inserted p-quinoid ring-I: Diphenyl-p-tropylphenylmethyl cation formed on an attempted preparation of 1 -cycloheptatrienylidene-4-diphenyl-methylidene-2,5-cyclohexadiene. Tetrahedron. 1974. V. 30. P. 2191- 2195. DOI: 10.1016/S0040-4020(01)97357-0.
5. Sanechika K., Kajigaeshi S., Kanemasa S. Azafulvenes; 51. A Facile Synthesis of 8-Azaheptafulvenes. Synthesis. 1977. N 3. P. 202-204. DOI: 10.1055/s-1977-24325.
6. Юнникова Л.П., Лихарева Ю.Л. Акентьева Т.А. Электрофильное 2-аминопиримидина. ЖОХ. 2017. Т. 87. № 2. С. 333-335.
7. Lyons D.J.M., Crocked R.D., Blumel, M., Nguyen, T.V. Promotion of Organic Reactions by Non-Benzenoid Carbo-cyclic Aromatic Ions. Angew. Chem., Int. Ed. 2017. V. 56. N 6. P. 1466-1484. DOI: 10.1002/anie.201605979.
8. Stanovnik B., Svete J. The Synthesis of Aplysinopsins, Meridianines, and Related Compounds. Mini-Reviews in Org. Chem. 2005. V. 2. N 3. P. 211-224. DOI: 10.2174/1570193054368864.
9. Fresneda P.M., Molina P., Delgado S., Bleda J.A. Synthetic studies towards the 2-aminopyrimidine alkaloids variolins and meridianins from marine origin. Tetrahedron Lett. 2000. V. 41. N 24. P. 4777-4780. DOI: 10.1016/S0040-4039(00)00728-0.
10. Sudhahar S., Krishna Kumar M., Silambarasan A., Muralidharan R. and Mohan Kumar R. Studies on Structural, Spectral, and Optical Properties of Organic Nonlinear Optical Single Crystal: 2-Amino-4,6-dimethyl-pyrimidinium p-Hydroxybenzoate. J. of Materials. 2013. P. 1-7. DOI: 10.1155/2013/539312.
11. Balasubramani K., Muthiah P. T., RajaRam R.K. and Sridhar B. Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidine-cinnamic acid (1/2). Acta Cryst. 2005. E. 61. P. 4203-4205. DOI: 10.1107/S160053680503730X.
2-(N-cydohepta-2',4',6'-triene-1'-ilamino)-3-(cydohepta-2',4',6'-triene-1'-il)-6-hydroxypyri-midin-4(3H)one 8. A 0.033 g portion (0.18 mmol) of salt 2 was added at one go to 0.04 g (0.18 mmol) of compound 6 suspended in 5 ml of ethanol while stirred. 10 Min later, the suspension colored white turned yellow. 2 H later, the reaction mass was treated with 10% solution of NH3 to attain pH 7. The yellow sediment was separated and rinsed with hexane and ether. Yield: 0.05 g (89%), m.p.190 °C (with decomposition).
REFERENCES
1. Yunnikova L.P. Hydroalkylation of imines by cyclohepta-1,3,5-trien. Mendeleev Comm. 1996. N 3. P. 25-26.
2. Yunnikova L.P., Akentieva T.A., Makhova T.V. One-pot three synthesis of N-arylmethyl-4-(7-cyclohepta-1.3.5-trienyl)anilines. Int. J. Organic Chem. 2013. V. 3. N 2. P. 148-150. DOI: 10.4236/ijoc.2013.32017.
3. Yunnikova L.P., Akentieva T.A., Esenbaeva V.V. Tro-pylation of Arylamines and Antimicrobial Activity of 4-(7-Cyclohepta-1,3,5-trienyl)-iV-(1-cyclohepta-2,4,6-trienyl)ani-line. Pharm. Chem. J. 2015. V. 49. N 4. P. 243-245. DOI: 10.1007/s11094-015-1263-3.
4. Takahashi K., Takenaka S., Nozoe T. Cyclic cross-conjugated hydrocarbons having inserted p-quinoid ring-I: Diphenyl-p-tropylphenylmethyl cation formed on an attempted preparation of 1 -cycloheptatrienylidene-4-diphenyl-methylidene-2,5-cyclohexadiene. Tetrahedron. 1974. V. 30. P. 2191- 2195. DOI: 10.1016/S0040-4020(01)97357-0.
5. Sanechika K., Kajigaeshi S., Kanemasa S. Azafulvenes; 51. A Facile Synthesis of 8-Azaheptafulvenes. Synthesis. 1977. N 3. P. 202-204. DOI: 10.1055/s-1977-24325.
6. Yunnikova L.P., Likhareva Yu.E., Akentieva T.A. Electro-philic tropylation of 2-aminopyridineine. J. General Chem. 2017. V. 87. N 2. P. 347-349. DOI: 10.1134/S1070363217020323.
7. Lyons D.J.M., Crocked R.D., Blumel, M., Nguyen, T.V. Promotion of Organic Reactions by Non-Benzenoid Carbo-cyclic Aromatic Ions. Angew. Chem., Int. Ed. 2017. V. 56. N 6. P. 1466-1484. DOI: 10.1002/anie.201605979.
8. Stanovnik B., Svete J. The Synthesis of Aplysinopsins, Meridianines, and Related Compounds. Mini-Reviews in Org. Chem. 2005. V. 2. N 3. P. 211-224. DOI: 10.2174/1570193054368864.
9. Fresneda P.M., Molina P., Delgado S., Bleda J.A. Synthetic studies towards the 2-aminopyrimidine alkaloids variolins and meridianins from marine origin. Tetrahedron Lett. 2000. V. 41. N 24. P. 4777-4780. DOI: 10.1016/S0040-4039(00)00728-0.
10. Sudhahar S., Krishna Kumar M., Silambarasan A., Muralidharan R. and Mohan Kumar R. Studies on Structural, Spectral, and Optical Properties of Organic Nonlinear Optical Single Crystal: 2-Amino-4,6-dimethyl-pyrimidinium p-Hydroxybenzoate. J. of Materials. 2013. P. 1-7. DOI: 10.1155/2013/539312.
11. Balasubramani K., Muthiah P. T., RajaRam R.K. and Sridhar B. Hydrogen-bonding patterns in 2-amino-4,6-dimethylpyrimidine-cinnamic acid (1/2). Acta Cryst. 2005. E. 61. P. 4203-4205. DOI: 10.1107/S160053680503730X.
12. Kitamura T., Hikita A., Ishikawa H., Fujimoto A. Pho-toinduced amino-imino tautomerization reaction in 2-
12. Kitamura T., Hikita A., Ishikawa H., Fujimoto A. Pho-toinduced amino-imino tautomerization reaction in 2-aminopyrimidine and its methyl derivatives with acetic acid. Spectrochimica Acta. 2005. V. 62. N 4-5. P. 1157-1164. DOI: 10.1016/j.saa.2005.04.008.
13. Sun D., Yuan S., Liu S.-S., Zhao Y.-Q., Han L.-L., Wang X.-P. Mixed Linker Strategy for the Construction of a Fluorescent 2D Network Based on [Ag2(COO)2] as Secondary Building Unit. Z. Naturforsch. 2013. V. 68. N 4. P. 357-361.
14. Fouda A.S., Abdallah Y.M. and Nabil D. Dimethyl Py-rimidine Derivatives as Corrosion Inhibitors for Carbon Steel in Hydrochloric Acid Solutions. IJIRSET. 2014. V. 3. N 5. P. 12965-12982.
15. Giulia O., Sander D. de Vos, Kevin N.H. Luc, Jason B.H., and Thanh V.N. Tropylium-Promoted Oxidative Func-tionalization of Tetrahydroisoquinolines. J. Org. Chem. 2018. V. 83. P. 1000-1010. DOI: 10.1021/acs.joc.7b02584.
16. Королева Е.В., Гусак К.Н., Игнатович Ж.В. Синтез и применение производных 2-аминопиримидина в качестве ключевых интермедиатов химического синтеза биомолекул. 2010. Т. 79. № 8. С. 720-746.
17. Королева Е.В., Игнатович Ж.И., Синютич Ю.В., Гусак К.Н. Производные аминопиримидина как ингидито-ры протекиназ. Молекулярный дизайн, синтез и биологическая активность. ЖОрХ. 2016. Т. 52. № 2. С. 159-196.
18. Галкина И.В., Галкин В.И., Юсупова Л.М., Губай-дуллин А.Т. Синтез, строение и биологическая активность продуктов реакций динитродихлорбензофурокса-на с аминопиримидинами в водном диметилсульфокси-де. 2016. Т. 52. № 5. С. 734-739.
19. Навроцкий М.Б. Синтез, противовирусная и цитоток-сическая активность 2-(алкилтио)-6-бензгидрид-4(3Н)-пиримидинов.Хи.м.-фар/и. ж. 2003. Т. 37. № 9. С.22-24.
20. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014. CrysAlis171 .NET).
21. Sheldrick G.M. A short history of SHELX. ActaCryst. 2008. A64. P 112-122. DOI: 10.1107/S0108767307043930.
aminopyrimidine and its methyl derivatives with acetic acid. Spectrochimica Acta. 2005. V. 62. N 4-5. P. 1157-1164. DOI: 10.1016/j.saa.2005.04.008.
13. Sun D., Yuan S., Liu S.-S., Zhao Y.-Q., Han L.-L., Wang X.-P. Mixed Linker Strategy for the Construction of a Fluorescent 2D Network Based on [Ag2(COO)2] as Secondary Building Unit. Z. Naturforsch. 2013. V. 68. N 4. P. 357-361.
14. Fouda A.S., Abdallah Y.M. and Nabil D. Dimethyl Py-rimidine Derivatives as Corrosion Inhibitors for Carbon Steel in Hydrochloric Acid Solutions. IJIRSET. 2014. V. 3. N 5. P. 12965-12982.
15. Giulia O., Sander D. de Vos, Kevin N.H Luc, Jason B.H., and Thanh V.N. Tropylium-Promoted Oxidative Func-tionalization of Tetrahydroisoquinolines. J. Org. Chem. 2018. V. 83. P. 1000-1010. DOI: 10.1021/acs.joc.7b02584.
16. Koroleva E.V., Gusak K.N., Ignatovich Z.V. Synthesis and applications of 2-aminopyrimidine derivatives as key intermediates in chemical synthesis of biomolecules. Russian Chem. Reviews. 2010. V. 79. N 8. P. 655-681. DOI: 10.1070/RC2010v079n08ABEH004116.
17. Koroleva E.V., Ignatovich Zh.I., Sinyutich Yu.V., Gusak K.N. Aminopyrimidine derivatives protein kinases inhibitors. Molecular design, synthesis, and biologic activity. J. Org. Chem. 2016. V. 52 N 2. P. 139-177. DOI: 10.1134/S1070428016020019.
18. Galkina IV., Galkin V.I, Yusupova L.M., Gubaidullin A.T. Synthesis, structure, and biologic activity of products of reactions between dinitrodichlorobenzofuroxane and aminopyrimidines in aqueous dimethyl sulfoxide. J. Org. Chem. 2016. V. 52. N 5. P. 734-739. DOI: 10.1134/S1070428016050201.
19. Navrotskii M.B. Synthesis and Study of the Antiviral and Cytotoxic Activity of 2-(Alkylthio)-6-benzhydryl-4(3H)-Pyrimidinones. Pharm. Chem. J. 2003. V. 37. N 9. P. 473-475. DOI: 10.1023/B:PHAC.0000008247.45050.60.
20. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014. CrysAlis171 .NET).
21. Sheldrick G.M. A short history of SHELX. ActaCryst. 2008. A64. P 112-122. DOI: 10.1107/S0108767307043930.
Поступила в редакцию 27.04.2018 Принята к опубликованию 09.07.2018
Received 27.04.2018 Accepted 09.07.2018
