Reatividade de (E)3-fenil-2H-azirinas-2-acrilatos com amidinas

AUTOR(ES)
DATA DE PUBLICAÇÃO

1987

RESUMO

2H-azirinas have received attetion as important intermediates in order to sinthesize new heterocyclic systems. In the presente work, the reativity of methyl-(E)-3-phenyl-2H- azirine-2-acrylate (38a) and methyl-(E)-3-phenyl-2-methyl-2H-azirine-2-acrylate (38b)systems toward amidines like formamidines (47a) and guanidine (47b) were investigated. Reactions of the disubstituted systems 38a with 47a and 47b afford 2-phenyl-4-methyle-acrylate-1H-imidazole (80) and 2-amino-4- phenyl-s-triazine-6-methyle-propionate (87), respectivelly. The leading to 2-phenyl-4-methyl-pirimidine-5-methyle-acetate (95) and 2- phenyl-4-methyl-pirimidine-5-acetamide (97) with the former and bicycle 2-amlno-4-phenyl-8a-methyl-6,7.8,8a-tetrahidro-pirrolo-[1,2-a]-6- one-1,3,5-triazine (90) or (91) with the later. There is a change is the reaction pathways whether the 2H-azirine is disubstituted 38a or tri substituted 38b. DMSO as the solvent plays an important role in these reactions, once it is noticed that the formation of 3-phenyl-1H-1,2,4-triazole-3- propionate-methyl (105) is observed, when reacting 38a with hydrazine. In order to investigate the reactivity of the systems 38a, 38b, 2H-azirine-2-formyl-substituted 36a e 36b, reactions with some specific nucleophiles (pseudothiurea, 106, 107 e 108; piridine N-imine (117) and 2-amino-benzimidazole (111) were accomplished. Moreover it was attempptted to obtaln reduction products from the reaction between 2H-azirines 38a and 38b with magnesium metal and sodium borohidride. The structures of all the products were elucidated on the basis of spectroscopia data associated with chemlcal transformations. Also the mechanisms for the transformations were proposed.

ASSUNTO(S)

reações quimicas reatividade (quimica)

ACESSO AO ARTIGO

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