151797-83-0Relevant articles and documents
Reactions of 3-diazo-1,3-dihydro-2H-indol-2-one derivatives with enaminones. A novel synthesis of 1,2,3-triazoles
Augusti,Kascheres
, p. 7079 - 7083 (1993)
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 1 (X = NR3) and 3-diazobenzo[b]thiophen-2(3H)-one 5 (X = S) with enaminones 2 and 7 leads to the formation of mainly 1,2,3-triazoles 4 and pyrazoloquinazolinones 3. Both the phenyl substituents (Y and Z in 1) and the nature of the X group affects 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 Ig is shown to be the most efficient in promoting 1,2,3-triazole 4 formation while pyrazoloquinazolinones 3 are often competitively formed when other derivatives of 1 are employed.
Preparation of Novel 1,2,3-Triazoles and a Comparative Study Involving Two Recent Methods for 1,2,3-Triazole Synthesis
Ferreira Melo, Julio Onesio,Ratton, Patricia Melo,Augusti, Rodinei,Donnici, Claudio Luis
, p. 369 - 376 (2004)
The syntheses of three novel 1,2,3-triazoles and a comparative study involving two recent methods of 1,2,3-triazole synthesis by diazo group transfers to enaminones, 5,7-dinitro-3-diazo-isatine and mesyl azide, are described. It was observed that the former is the more general and promising method for the synthesis of any 1,2,3-triazole but, when both methods work the mesyl azide one generally gives better yields.
