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

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

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.

Full Text

Restricted Access

About the authors

S. O. Kushch

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

Author for correspondence.
Email: pmv@ios.uran.ru
ORCID iD: 0000-0002-7518-8998
Russian Federation, Ekaterinburg

M. V. Goryaeva

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

Email: marinavgoryaeva@gmail.com
ORCID iD: 0000-0002-7853-688X
Russian Federation, Ekaterinburg

E. A. 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
Russian Federation, Ekaterinburg

Ya. V. 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
Russian Federation, Ekaterinburg

V. I. 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
Russian Federation, Ekaterinburg

References

  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

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. 1. SSCC of diastereotopic protons in heterocycles 4, 6, 7

Download (134KB)
Indexing metadata
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

Download (106KB)
Indexing metadata
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

Download (107KB)
Indexing metadata
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

Download (103KB)
Indexing metadata
6. Scheme 1

Download (94KB)
Indexing metadata
7. Scheme 2

Download (93KB)
Indexing metadata
8. Scheme 3

Download (213KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences