130698-48-5Relevant academic research and scientific papers
Reaction of Methyl (E)-2-Phenyl-1-azirine-3-acrylates with Hydrazines and Amidines. Synthetic and Mechanistic Implications
Kascheres, Albert,Oliveira, Cecilia M. A.,Azevedo, Mariangela . M. de,Nobre, Cintia M. S.
, p. 7 - 9 (2007/10/02)
1-Azirines 2a-b react with hydrazine in methanol to produce hexahydropyrrolopyrazol-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.
