INVESTIGADORES
SORIA CASTRO Silvia Mercedes
artículos
Título:
Thermal ring opening of pyrazolo[3,4-d][1,2,3]triazin-4-ones: an experimental and theoretical study
Autor/es:
COLOMER, JUAN PABLO; SCIÚ, MARÍA LOURDES; RAMIREZ, CRISTINA; SORIA CASTRO, SILVIA; VERA, DOMINGO MARIANO; MOYANO, ELIZABETH LAURA
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Año: 2018
ISSN:
1434-193X
Resumen:
Several 3-pyrazolecarbonyl-pyrazolo[3,4-d][1,2,3]triazin-4-ones were prepared from 5-amino-1H-pyrazole-4-carbonitrilesthrough a simple sequence. In a first step, diazotization ofaminopyrazole afforded pyrazolo[3,4-d][1,2,3]triazin-4-ones. Next, athermal rearrangement of these compounds through a nitrogenelimination gave the final products. The proposed mechanism for thering opening of pyrazolotriazinones to give the pyrazolecarbonylpyrazolotriazinonesincludes the generation of an iminoketeneintermediate, which reacts with a second molecule ofpyrazolotriazinone. The complete and detailed mechanism of productformation involving the iminoketene intermediate and all otherreasonable pathways as well, were explored with DFT calculations.Furthermore, additional experimental studies to corroborate thepresence of iminoketene intermediate were carried out.
