Synthesis and Transformation into 4,5-Dihydroisoxazole Derivatives of Methyl(hetarylalkyl)-N-allyl-N-phenylcarbamates

Cover Page

Cite item

Full Text

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

Abstract

By alkylation of aromatic carbamates with allyl bromide under liquid-liquid phase transfer catalysis, the corresponding N-allyl derivatives of aryl carbamates were obtained in 63–71% yields. It has been established that the cycloaddition of arene carbonitrile N-oxides, generated in situ from the corresponding oximes in the presence of chloramine T, to the allylic fragment upon boiling in ethanol leads to the production of the corresponding 4,5-dihydroisoxazole derivatives in 89–96% yields.

Full Text

Restricted Access

About the authors

A. V. Velikorodov

Astrakhan Tatishchev State University; Astrakhan State Medical University

Author for correspondence.
Email: avelikorodov@mail.ru
ORCID iD: 0000-0001-9802-8252
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000; ul. Bakinskaya, 121, Astrakhan, 414000

E. N. Kutlalieva

Astrakhan Tatishchev State University; Astrakhan State Medical University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0002-9712-4223
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000; ul. Bakinskaya, 121, Astrakhan, 414000

N. V. Zolotareva

Astrakhan Tatishchev State University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0002-3209-2929
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000

N. N. Stepkina

Astrakhan Tatishchev State University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0001-8603-3951
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000

S. B. Nosachev

Astrakhan Tatishchev State University

Email: avelikorodov@mail.ru
ORCID iD: 0000-0001-8469-5425
Russian Federation, pl. Shahumyana, 1, Astrakhan, 414000

References

  1. Ozoe Y., Asahi M., Ozoe F., Nakahira K., Mita T.Biochem. Biophys. Res. Commun. 2010, 391, 744-749. doi: 10.1016/j.bbrc.2009.11.131
  2. Andrade Danin Barbosa G., Aguiar A.P., Car-valho E.M., Rocha Nogueira J.M. Lett. Drug Des. Dis. 2019, 16, 364-369. doi: 10.2174/1570180815666180627115606
  3. Song D., Bi F., Zhang N., Qin Y., Liu X., Teng Y., Ma Sh. Bioorg. Med. Chem. 2020, 28, 115729. doi: 10.1016/j.bmc.2020.115729
  4. Jayashankara B., Lokanatha Rai K.M. ARKIVOC. 2008 (xi). 75-85. doi: 10.3998/ark.5550190.0009.b07
  5. Patel A.J., Patel M.P. Indian J. Adv. Chem. Sci. 2016, 4, 409-420.
  6. Alshamari A., Al-Qudah M., Hamadeh F., Al-Momani L., Abu-Orabi S. Molecules. 2020, 25, 4271. doi: 10.3390/molecules25184271
  7. Molina C.Τ., Aguiar A.P. Ηeterocycl. Commun. 2003, 9, 535-538. doi: 10.1515/HC.2003.9.5.535
  8. Maksimenko A.S., Kislyi V.P., Chernysheva N.B., Strelenko Yu.A., Zubavichus Ya.V., Khrustalev V.N., Semenova M.N., Semenov V.V. Eur. J. Org. Chem. 2019, 4260-4270. doi: 10.1002/ejoc.201900643
  9. Kumar K.A., Lokeshwari D.M., Kumar G.V. Int. J. Pharm. Sci. Drug Res. 2012, 4, 236-239.
  10. Kamal A., Bharathi E.V., Reddy J.S., Ramaiah M.J., Dastagiri D., Reddy K.M., Viswanath A., Reddy T.L., Shaik T.B., Pushpavalli S.N.C.V.L., Bhadra M.P. Eur. J. Med. Chem. 2011, 46, 691–703. doi: 10.1016/j.ejmech.2010.12.004
  11. Putarov N.B., Cruz J.S., Carvalho E.M., Mendonça D.S., Sampaio A.L.F., Nogueira J.M.R., Costa G.L., Aguiar A.P. Rev. Virtual Quim. 2020, 12, 345-355.
  12. Sun R.D., Lee R.B., Tangallapally R.P., Lee R.E. Eur. J. Med. Chem. 2009, 44, 460–472. doi: 10.1016/j.ejmech.2008.04.007
  13. Dafik L., Khosla C. Chem.Biol. 2011, 18, 58–66. doi: 10.1016/j.chembiol.2010.11.004
  14. Ros A., Alvarez E., Dietrich E., Fernández R., Lassaletta J.M. Synlett. 2005, 2899–2904. doi: 10.1055/s-2005-921894
  15. Вафина Г.Ф., Мухамедьянова А.А., Ханова М.Д., Спирихин Л.В. ХГС. 2018, 54, 796–803. [Vafina G.F., Mukhamed′yanova A.A., Khanova M.D., Spirikhin L.V. Chem. Heterocycl. Compd. 2018, 54, 796-803]. doi: 10.1007/s10593-018-2352-5
  16. Al-Abbasee M.J.T., Al-Hilali B.M.I., Hussein A.K. Int. J. Rec. Sci. Res. 2018, 9, 24738-24744. doi: 10.24327/ijrsr.2018.0903.1718
  17. Abbas A.F., Turki A.A., Hameed A.J. J. Mater. Environ. Sci. 2012, 3, 1071-1078.
  18. Samshuddin S., Butcher R.J., Akkurt M., Narayana B., Yathirajand H.S. Acta Cryst. 2011, E67, o1975-o1976. doi: 10.1107/S1600536811026833
  19. Bhardwaj S., Bendi A., Singh L. Curr. Org. Synth. 2022, 19, 643-663. doi: 10.2174/1570179419666220127143141
  20. Abdul-Bary M., Hadd B. 2nd Int. Conf. Mat. Eng. Sci. (IConMEAS 2019) AIP Conf. Proc. 2020, 2213, 020091-1. doi: 10.1063/5.0000320
  21. Виноградов А.Н., Козьминых В.О., Козьминых Е.Н. Башкирский хим. ж. 2014, 21, 104-106.
  22. Zielinska-Błajet M., Kowalczyk R., Skarzew-ski J. Tetrahedron. 2005, 61, 5235–5240. doi: 10.1016/j.tet.2005.03.085
  23. Chernysheva N.B., Maksimenko A.S., Andreya-nov F.A., Kislyi V.P., Strelenko Yu.A., Khrustalev V.N., Semenova M.N., Semenov V.V. Tetrahedron. 2017, 73, 6728-6735. doi: 10.1016/j.tet.2017.10.016
  24. Великородов А.В., Мочалин В.Б. ЖОрХ, 2001, 37, 93-96 [Velikorodov A.V., Mochalin V.B. Russ. J. Org. Chem. 2001, 37, 83-86]. doi: 10.1023/A:1012329518308
  25. Великородов А.В., Бакова О.В., Мочалин В.Б. ЖОрХ. 2002, 38, 72-74 [VelikorodovA.V., BakovaO.V., Mochalin V.B. Russ. J. Org. Chem. 2002, 38, 66-69]. doi: 10.1023/A:1015302724908
  26. Bogdanov V.S., Aitzhanova M.A., Abronin I.A., Medvedskaya A.B. Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 305-316.
  27. Chrisope D.R., Keel R.A., Baumstark A.L., Boykin D.W. J. Heterocycl. Chem. 1981, 18, 795-798. doi: 10.1002/jhet.5570180433
  28. Barnet K. Angew. Chem. 1985, 97, 231-232. doi: 10.1002/ange.19850970326
  29. Kondo Y., Uchiyama D., Sakamoto T., Yamanaka H. Tetrahedron Lett. 1989, 30, 4249-4250.

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Scheme 1 1a–h, 2a–h: R = Me, R' = H (a); R = Me, R' = 4-Meo (b); R = Me, R' = 4-MeO (c); R = Me, R' = 4-NO2 (d); R = Me, R' = 4-Br(e); R = 2-furylmethyl, R' = H(f), R= 2-morpholinoethyl, R' = H(g); R = 2-(pyridine-2-Yl)ethyl (I).

Download (49KB)
Indexing metadata
3. Scheme 2 2a–f, 3a–f: R = Me, R' = H, Ar = 3-NO2C6H4 (a); R = Me, R' = H, Ar = 3,4-OCH2OC6H3 (b); R = Me, R' = 4-Me, Ar = 4-BrC6H4 (c); R = Me, R' = 4-MeO, Ar = 4-MeOC6H4 (d); R = 2-furanmethyl, R' = H, AR = 4-meoc6h4 (E); R = 2-Furanmethyl, R' = H, AR = 3-No2c6h4 (F); R = me, R' = 4-NO2, AR = 4-Meoc6h4 (G)

Download (62KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences