INVESTIGADORES
VERA Domingo Mariano Adolfo
artículos
Título:
Thermal ring opening of pyrazolo[3,4-d][1,2,3]triazin-4-ones: an experimental and theoretical study
Autor/es:
J. P. COLOMER; M. L. SCIU; C. L. RAMIREZ; S. M. SORIA CASTRO; D. M. A. VERA*; E. L. MOYANO
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Lugar: Weinheim; Año: 2018 vol. 2018 p. 1514 - 1524
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 pyrazolecarbonyl-pyrazolotriazinones includes 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.