Estudo da reatividade de "alfa"-diazocetonas heterociclicas frente a enaminomas : obtenção de triazois

AUTOR(ES)

Rodinei Augusti

DATA DE PUBLICAÇÃO

1990

RESUMO

The reactions of 3-diazo-1,3-dihydro-1-methyl-2H-indol-2-one (11) with acyclic enaminones RCOCH=C(CH3)NRR (2) (2a: R= R= Me; R= H and 2e:R= Me; R = R= H) provided compound 16 (16a. 2-acetyl-1,6-dlmethylpyrazol-[1,5c]-quinazoline-5(6H)-one or 16b:1-acetyl-2,6-dimethylpyrazol-[1.5c]-quinazoline-5(6H)-one) in low yields, which is analogous to compound 10 formed previously Structure confirmation of compound 10 (10a: 2-acetyl-1-methylpyrazol-[1,5c]-quinazoline-5(6H)-one or 10b: 1-acetyl-2 methylpyrazol]-[1,5c]-quinazoline-5(6H)-one) by spectroscopic analysis of the reduced compound, did not provide definitive results. The reactions of 3-diazo-benzo-[b]-thiophen-2(3H)-one (12) with acyclic 2 (2a-d) and cyclic 6 (6a-b) enaminones provided triazoles 17, through novel N2 transference from diazoketone 12 to enaminones 2 and 6. The yields varied depending on the nitrogen or carbonyl substituents. Frontier moIecular orbital theory provided coherent explanations about differences in behavior between diazoketone 12 and its anaIogous 11 and 9 (9: 3-diazo-1,3-dihydro-2H-indol-2-one). In fact, it was possible to expIain the difference in yields observed in the triazole synthesis. Thus, this theory proved to be useful in the investigation of several aspects involved in this reaction.

ASSUNTO(S)

compostos de diazo

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