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

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...

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Bibliographic Details
Published in:Tetrahedron 2014-06, Vol.70 (25), p.3915-3923
Main Authors: Beryozkina, Tetyana V., Zhidovinov, Sergey S., Shafran, Yuri M., Eltsov, Oleg S., Slepukhin, Pavel A., Leban, Johann, Marquez, Javier, Bakulev, Vasiliy A.
Format: Article
Language:English
Subjects:
1,3,5-Triisoxazolyl benzenes
Acetyl chloride
Dieneamines
Enamines
Formations
Isoxazoles
Self-condensation
Solvents
Spectra
Synthesis (chemistry)
Tetrahedrons
Two dimensional
X-rays
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.04.015