Desenvolvimento de um metodo novo e geral de sintese de 1, 2, 3-triazois a partir do estudo da reatividade de compostos diazoisatinicos frente a enaminonas

AUTOR(ES)

Rodinei Augusti

DATA DE PUBLICAÇÃO

1993

RESUMO

A new and efficient method of 1,2,3-triazole synthesis is described in which these heterocyclics are formed through a novel nitrogen transfer from diazocarbonyl compounds to enaminones. Thus, the reaction of 3-diazo-1,3-dihydro-2H-indol-2-one derivatives (75) with enaminones (76, 82 and 81) leads to the formation of mainly 1,2,3-triazoles (77, 95 and 96) and pyrazoloquinazolinones (78). The phenyl substituents (Y and Z in 75) affect the reaction rate and product distribution. Rate increases with an increase in the electron-withdrawing ability of the substituents Y and Z. The dinitro derivative (75h) is shown to be the most efficient in promoting 1,2,3-triazole (77, 95 and 96) formation while pyrazoloquinazolinones (78) are often competitively formed when other derivatives of 75 are employed. Frontier molecular orbital theory provides coherent explanations about differences in behavior between diazocarbonyl compounds 75 and it proves to be useful in the investigation of several aspects of this reaction.

ASSUNTO(S)

compostos de diazo orbitais moleculares

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