Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/58929
Type: Artigo de periódico
Title: REACTION OF METHYL (E)-2-PHENYL-1-AZIRINE-3-ACRYLATES WITH HYDRAZINES AND AMIDINES - SYNTHETIC AND MECHANISTIC IMPLICATIONS
Author: KASCHERES, A
OLIVEIRA, CMA
DEAZEVEDO, MBM
NOBRE, CMS
Abstract: 1-Azirines 2a-b react with hydrazine in methanol to produce hexahydropyrrolo[3,2-c]pyrazol-5-ones 3a-b. The process is suggested to involve intramolecular interception of an unstable 4-aminopyrazoline intermediate resulting from C=N bond cleavage. Reaction of 2a with phenylhydrazine similarly affords 3c. In dimethyl sulfoxide, on the other hand, formamidine, guanidine, and hydrazine afford imidazole 4, pyrimidines 5a-b, amino-s-triazine 6, or triazole 9 as a consequence of C-C bond cleavage in aziridine intermediate 8. The intermediacy of tautomers is proposed to account for the diversity of products in this case.
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/jo00001a004
Date Issue: 1991
Appears in Collections:Unicamp - Artigos e Outros Documentos

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