Reatividade de enaminotionas frente a derivados de 1-Azirina e de difenilciclo-propenona

AUTOR(ES)
DATA DE PUBLICAÇÃO

1987

RESUMO

The reactivity of aliphatic enaminothiones (1) with microcyclic compounds (diphenylcyclopropenone (2) and 1-azirine derivatives (3)) was tested. Four enaminothiones were synthetized (1a-1d): one primary (4-amino-3-penten-2-thione (1a)) , two secondaryes (4-anilino-3-penten-2-thione (1b) and 4-benzylamino-3-penten-2-thione (1c)) and one tertiary (4-pirrolidino-3-penten-2-thione (1d)),unknown in the literature. The methods used to obtain these compounds were the transformation of correspoding enaminones using P2S5 or Lawesson reagent (70). These reactions with both enaminothiones (1) and diphenylcyclopropenone (2) showed a nucleophilic caracter of the alfa carbon to C=S (which is not reported in the literature.These reactions produce unknown enaminones (95) which is a result of the coupling of one molecule of 1 with one molecule of 2 with lost of ,H2S (it is not reported in the literature for enaminothione (1) reactions). Diphenylcyclopropenone (2) showed diferent chemical behavior than those given in the literature for reactions of 2 with analogous systems. The reactions with both 1 and 1-azirine derivatives (3) produced componds of [4+2] cycloadditions. These products, depended on the nitrogen substituent, might undergo intramolecular cyclization, producing new heterocyclic compounds. The structures were estabilished by spectroscopic methods and chemical reactions. For these reaction mechanisms were propesed.

ASSUNTO(S)

cetonas reatividade (quimica)

ACESSO AO ARTIGO

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