Multicomponent Cyclizations of Ethyl Trifluoroacetoacetate with Acetaldehyde and 1,3-Diamines to Heteroannulated Pyridines

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

A four-component approach was developed for the synthesis of cis- and trans-diastereomeric partially hydrogenated pyrido[1,2-a]pyrimidines and pyrido[2,1-b]quinazolines based on the cyclization of ethyl trifluoroacetoacetate with two acetaldehyde molecules and 1,3-diaminopropane or 2-aminomethylaniline. The zwitterionic salt of tetrahydropyrimidine was isolated as a by-product from the reaction with 1,3-diaminopropane. And from the reaction with 2-aminomethylaniline 7-hydroxy-7-(trifluoromethyl)-5,5a,6,7,8,11-hexahydro-9H-pyrido[2,1-b]quinazolin-9-one was obtained as a result of the participation of one aldehyde molecule. The diastereomeric structure of the synthesized heterocycles was established on the basis of 1Н, 19F, 13С NMR spectroscopy and XRD. A mechanism for the formation of new heteroannulated pyridines was proposed.

Texto integral

Acesso é fechado

Sobre autores

S. Kushch

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Autor responsável pela correspondência
Email: pmv@ios.uran.ru
ORCID ID: 0000-0002-7518-8998
Rússia, Ekaterinburg

M. Goryaeva

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: marinavgoryaeva@gmail.com
ORCID ID: 0000-0002-7853-688X
Rússia, Ekaterinburg

E. Surnina

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: pmv@ios.uran.ru
ORCID ID: 0000-0003-2961-6450
Rússia, Ekaterinburg

Ya. Burgart

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: pmv@ios.uran.ru
ORCID ID: 0000-0001-6061-2410
Rússia, Ekaterinburg

V. Saloutin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: pmv@ios.uran.ru
ORCID ID: 0000-0003-1976-7861
Rússia, Ekaterinburg

Bibliografia

  1. Zhu J., Bienayme H., Multicomponent Reactions, Wiley-VCH Weinheim, Germany, 2005.
  2. Ganem. B. Acc. Chem. Res. 2009, 42, 463–472. doi: 10.1021/ar800214s
  3. Karnakar K., Ramesh K., Reddy K.H.V., Anil Kumar B.S.P., Nanubonula J.B., Nageswar Y.V.D. New J. Chem. 2015, 39, 8978–8983. doi: 10.1039/C5NJ01448D
  4. Gibadullina N.N., Latypova D.R., Novikov R.A., Tomilov Y.V., Dokicheva V.A. Arkivoc 2017, 222–235. doi: 10.24820/ark.5550190.p010.003
  5. Zhou L., Yuan F., Zhou Y., Duan W., Zhang M., Deng H., Song L. Tetrahedron 2018, 74, 3761–3769. doi: 10.1016/j.tet.2018.05.059
  6. Bhatt J.D., Patel T.S., Chudasama C.J., Patel K.D. ChemistrySelect 2018, 3, 3632–3640. doi: 10.1002/slct.201702285
  7. Dayakar C., Raju B.C., ChemistrySelect, 2018, 3, 9388–9392. doi: 10.1002/slct.201801430
  8. Du X.-X., Zi Q.-X., Wu Y.-M., Jin Y., Lin J., Yan S.-J. Green Chem. 2019, 21, 1505–1516. doi: 10.1039/C8GC03698E
  9. Бургарт Я.В., Кузуева О.Г., Прядеина М.В., Каппе С.О., Салоутин В.И. ЖОрХ, 2001, 37, 915–926. [Burgart Ya.V., Kuzueva O.G., Pryadeina M.V., Kappe C.O., Saloutin V.I. Russ. J. Org. Chem. 2001, 37, 869–880.] doi: 10.1023/A:1012473901354
  10. Shashi R., Prasad N.L., Begum N.S. J. Struct. Chem. 2020, 61, 938–947. doi: 10.1134/s0022476620060141.
  11. Goryaeva M.V., Kushch S.O., Khudina O.G., Burgart Ya.V., Ezhikova M.A., Kodess M.I., Slepukhin P.A., Volobueva A.S., Slita A.V., Esaulkova I.L., Misiurina M.A., Zarubaev V.V., Saloutin V.I. J. Fluor. Chem. 2021, 241, 109686. doi: 10.1016/j.jfluchem.2020.109686
  12. Kushch S.O., Goryaeva M.V., Burgart Ya.V., Ezhikova M.A, Kodess M.I., Slepukhin P.A., Saloutin V.I. Asian J. Org. Chem., 2022, 11, e202100709. doi: 10.1002/ajoc.202100709
  13. Smith R.L., Barrett R. J., Sanders-Bush E., J. Pharmacol. Exp. Ther. 1995, 275, 1050–1057.
  14. Meltzer H.Y., Simonovic M., Gudelsky G.A. Eur. J. Pharmacol. 1983, 92, 83–89. doi: 10.1016/0014-2999(83)90111-5
  15. Awouters F., Vermeire J., Smeyers F., Vermote P., Van Beek R., Niemegeers C.J.E. Drug. Dev. Res. 1986, 8, 95–102. doi: 10.1002/ddr.430080112
  16. Yanagihara Y., Kasai H., Kawashima T., Shida T. Jpn. J. Pharamacol. 1988, 48, 91–101. doi: 10.1254/jjp.48.91
  17. Shakhidoyatov K.M., Elmuradov B. Z., Chem. Nat. Compd. 2014, 50, 781–800. doi: 10.1007/s10600-014-1086-6
  18. Kshirsagar U.A. Org. Biomol. Chem. 2015, 13, 9336–9352. doi: 10.1039/c5ob01379h
  19. Jeffries B., Wang Z., Graton J., Holland S.D., Brind T., Greenwood R.D.R., Le Questel J.Y., Scott J.S., Chiarparin E., Linclau B. J. Med. Chem., 2018, 61, 10602–10618. doi: 10.1021/acs.jmedchem.8b01222
  20. Преч Э., Бюльманн Ф., Аффольтер К., Определение строения органических соединений, пер. с англ. Б.Н. Тарасевича, Мир, Бином, Лаборатория знаний, Москва, 2006. doi: 10.1007/978-3-662-04201-4
  21. Hill R.K., Carlson R.M. J. Am. Chem. Soc. 1965, 87, 2772–2773. doi: 10.1021/ja01090a054
  22. Atkinson, R. S. J. Chem. Soc. D. 1969, 13, 735. doi: 10.1039/c2969000735a
  23. Dolomanov O.V., Bourhis L.J., Gildea R.J., Ho-ward J.A.K., Puschmann H. J. Appl. Crystallogr. 2009, 42, 339–341. doi: 10.1107/S0021889808042726
  24. Sheldrick G.M. Acta Crystallogr., Sect. A: Cryst. Phys. 2008, 64, 112–122. doi: 10.1107/S0108767307043930

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Fig. 1. SSCC of diastereotopic protons in heterocycles 4, 6, 7

Baixar (134KB)
Metadados
3. Fig. 2. General view of the molecule of compound 4trans according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with 30% probability

Baixar (106KB)
Metadados
4. Fig. 3. General view of the molecule of compound 4cis according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with 30% probability

Baixar (107KB)
Metadados
5. Fig. 4. General view of the molecule of compound 5 according to X-ray diffraction data with atoms represented by thermal vibration ellipsoids with a 30% probability

Baixar (103KB)
Metadados
6. Scheme 1

Baixar (94KB)
Metadados
7. Scheme 2

Baixar (93KB)
Metadados
8. Scheme 3

Baixar (213KB)
Metadados

Declaração de direitos autorais © Russian Academy of Sciences, 2024