Heterocyclic thiones and their analogs in reactions of 1,3-dipolar cycloaddition: III. Reaction of benzothiazole-2-thione with a double excess of nitrilimine

Main products of reaction between benzothiazole-2-thione and a double excess of nitrilimine are substituted 1-aryl-1-(1,3-benzothiazol-2-yl)-2-(2,3-dihydro-1,3,4-thiadiazol-2-yl)hydrazines. In the first step presumably forms a spiro compound via 1,3-dipolar cycloaddition of nitrilimine molecule to t...

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Published inRussian journal of organic chemistry Vol. 40; no. 8; pp. 1175 - 1180
Main Authors Firsova, OV, Doigushina, TS, Polukeev, BA, Zavodnik, VE, Stash, AI, Bel'skii, VK, Galishev, VA
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.08.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Main products of reaction between benzothiazole-2-thione and a double excess of nitrilimine are substituted 1-aryl-1-(1,3-benzothiazol-2-yl)-2-(2,3-dihydro-1,3,4-thiadiazol-2-yl)hydrazines. In the first step presumably forms a spiro compound via 1,3-dipolar cycloaddition of nitrilimine molecule to the C=S bond of the benzothiazolethione. The second nitrilimine molecule adds to the new C=S bond of the intermediate product arising by the rupture of C-S bond in the thiadiazole ring of the spiro compound.
ISSN:1070-4280
1608-3393
DOI:10.1023/B:RUJO.0000045901.75965.de