Synthesis of novel fused azaheterocycles by photostimulated intramolecular SRN1 reactions with nitrogen nucleophiles

VICTORIA A. VAILLARD; MARÍA E. BUDÉN; SANDRA E. MARTÍN; ROBERTO A. ROSSI

TETRAHEDRON LETTERS

Elsiever

Lugar: Orlando; Año: 2009 vol. 50 p. 3829 - 3832

0040-4039

The synthesis of pyrrole, indole and pyrazole fused azaheterocycles is presented. The anion of carboxamides (6 and 12) and pyrazolylamines (15a-b) react under phtostimulation by SRN1 process to yield azaheterocycles with good to excellent yields. We report on an efficient two step synthesis of new fused azaheterocycles, deriver from pyrrole, indole and pyrazole as well as the synthesis of their precursors. By the reaction of carboxamides (6 and 12) and pyrazolylamines (15 a-b) with a base, the corresponding anion could be formed. Then by an intramolecular photostimulated SRN1 reaction, the fused azaheterocycles were achieved (54-100%).