Self-condensation of β-(isoxazol-5-yl) enamines under treatment with acetyl chloride and acids. Synthesis of novel 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes / Beryozkina T.V., Zhidovinov S.S., Shafran Y.M., Eltsov O.S., Slepukhin P.A., Leban J., Marquez J., Bakulev V.A. // Tetrahedron. - 2014. - V. 70, l. 25. - P. 3915-3923.

ISSN:

00404020

Type:

Article

Abstract:

Two directions for self-condensation of β-(isoxazol-5-yl) enamines under treatment with either acetyl chloride or acids were found leading to new 1,3-diisoxazolyl-1,3-dieneamines and 1,3,5-triisoxazolyl benzenes. The effect of solvent, acid, temperature and the reaction time on the ratio of reaction products were investigated. Trans-E-cis configuration of prepared 1,3-diisoxazolyl-1,3-dieneamines was unambiguously confirmed by 2D NMR spectra and X-ray analysis. A new mechanism of 1,3-diisoxazolyl-1,3-dieneamines formation was proposed. © 2014 Elsevier Ltd. All rights reserved.

Author keywords:

1,3,5-Triisoxazolyl benzenes; Dieneamines; Enamines; Isoxazoles; Self-condensation

Index keywords:

1,3 diisoxazolyl 1,3 dieneamine; 1,3,5 triisoxazolyl benzene; acetyl chloride; acid; benzene; beta (isoxazol 5 yl) enamine; enamine; isoxazole derivative; solvent; unclassified drug; article; carbon n

DOI:

10.1016/j.tet.2014.04.015

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-84900812692&doi=10.1016%2fj.tet.2014.04.015&partnerID=40&md5=d6e6191af5b8e6a742b782eb79312fff

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Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84900812692&doi=10.1016%2fj.tet.2014.04.015&partnerID=40&md5=d6e6191af5b8e6a742b782eb79312fff
Affiliations	TOS Department, Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira str., 620002 Ekaterinburg, Russian Federation; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Science, 20 S. Kovalevskaya str., 620990 Ekaterinburg, Russian Federation; Medicinal University of Vienna, Gert Lubec Proteomics Laboratory, 14 Lazarettgasse, 1090 Vienna, Austria; Department of Molecular Biology and Biochemistry, Faculty of Sciences, University of Malaga, 29071 Malaga, Spain
Author Keywords	1,3,5-Triisoxazolyl benzenes; Dieneamines; Enamines; Isoxazoles; Self-condensation
Chemicals/CAS	benzene, 71-43-2
Funding Details	14-03-01033, RFBR, Russian Foundation for Basic Research
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Correspondence Address	Bakulev, V.A.; TOS Department, Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira str., 620002 Ekaterinburg, Russian Federation; email: v.a.bakulev@urfu.ru
Publisher	Elsevier Ltd
CODEN	TETRA
Language of Original Document	English
Abbreviated Source Title	Tetrahedron
Source	Scopus