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

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

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Published inRussian journal of organic chemistry Vol. 53; no. 3; pp. 407 - 412
Main Authors Chornous, V. A., Mel’nik, O. Ya, Grozav, A. N., Suikov, S. Yu, Vovk, M. V.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 2017
Springer Nature B.V
Subjects
Chemical reactions
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:1-Aryl-4-chloro-5-(2-nitroethenyl)-1 H -imidazoles reacted with thiols and aromatic amines via Michael addition to give 5-[(1-arylsulfanyl)-2-nitroethyl)]-4-chloro-1 H -imidazoles and N -[1-(1-aryl-4-chloro-1 H -imidazol-5-yl)-2-nitroethyl]anilines, respectively. [2 + 3]-Cycloaddition of the title compounds to sodium azide afforded 4-(4-chloro-1 H -imidazol-5-yl)-1 H -1,2,3-triazoles.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428017030150