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Features and applications of reactions of α,β-unsaturated N-acylbenzotriazoles with amino compounds

Authors :
Lichun Kong
Xinsheng Li
Zhifang Li
Xiaoxia Wang
Xuefei Zou
Xiangming Zhu
Hui Mao
Source :
Tetrahedron. 64:6510-6521
Publication Year :
2008
Publisher :
Elsevier BV, 2008.

Abstract

Promoted by triethylamine, α,β-unsaturated N-acylbenzotriazoles reacted with amino compounds in a variety of ways. Thus, N-cinnamoylbenzotriazoles reacting with aromatic amines afforded novel addition products β-benzotriazolyl amides 3, which might be normally formed from the alternative but unknown 1,4-addition of benzotriazole to N-cinnamoylamides. The type 3 compounds could also result from the reaction between N-crotonoylbenzotriazole and aliphatic amines. However, normal 1,4-addition could occur between α,β-unsaturated aliphatic N-acylbenzotriazoles and aromatic amines, leading to β-amino N-acylbenzotriazoles 4 in good yields. In addition, exclusive 1,2-addition of aliphatic amines to N-cinnamoylbenzotriazoles gave excellent yields of cinnamides 5. Accordingly, three possible routes were proposed to rationalize the formation of compounds 3–5. Finally, with o-phenylenediamine and o-aminothiophenol as the substrates, the 1,4- and 1,2-addition to α,β-unsaturated N-acylbenzotriazoles could take place concurrently and the corresponding heterocycles 1,5-benzodiazepine-2-one and 1,5-benzothiazepine-4-one were constructed, respectively.

Details

ISSN :
00404020
Volume :
64
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........ded1efe435015137f8060510db3bbf57
Full Text :
https://doi.org/10.1016/j.tet.2008.04.054