Polyfunctional imidazoles: XIII. 1  Addition and cyclization reactions of 1-aryl-4-chloro-5-(2-nitroethenyl)-1 H -imidazoles with sulfur and nitrogen nucleophiles

V. A. Chornous; O. Ya. Mel’nik; A. N. Grozav; S. Yu. Suikov; M. V. Vovk

doi:10.1134/S1070428017030150

Polyfunctional imidazoles: XIII.¹ Addition and cyclization reactions of 1-aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles with sulfur and nitrogen nucleophiles

Authors: Chornous V.A.¹, Mel’nik O.Y.², Grozav A.N.¹, Suikov S.Y.³, Vovk M.V.³
Affiliations:
1. Bukovinian State Medical University
2. Ivano-Frankivsk National Medical University
3. Institute of Organic Chemistry
Issue: Vol 53, No 3 (2017)
Pages: 407-412
Section: Article
URL: https://journals.rcsi.science/1070-4280/article/view/215933
DOI: https://doi.org/10.1134/S1070428017030150
ID: 215933

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Abstract

1-Aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles reacted with thiols and aromatic amines via Michael addition to give 5-[(1-arylsulfanyl)-2-nitroethyl)]-4-chloro-1H-imidazoles and N-[1-(1-aryl-4-chloro-1H-imidazol-5-yl)-2-nitroethyl]anilines, respectively. [2 + 3]-Cycloaddition of the title compounds to sodium azide afforded 4-(4-chloro-1H-imidazol-5-yl)-1H-1,2,3-triazoles.