A convenient and efficient route for the chemoselective synthesis of carbohydrazide, arenesulfonylhydrazide, and thiosemicarbazone derivatives of 5H-pyrrolo[3,4-b]pyrazine and 1H-pyrrolo [3,4-b]quinoxaline from the corresponding dinitriles and substituted hydrazines was elaborated. The synthesis of starting pyrazine-2,3-dicarbonitrile was sufficiently improved by using concentrated HCl as a catalyst. pyrazine and 1H-Pyrrolo[3,4-b]quinoxaline 3377 © Georg Thieme Verlag Stuttgart · New York Synthesis 2013, 45, 3375-3382 O. V. Hordiyenko et al. PAPER Synthesis 2013, 45, 3375-3382 [3,4-b]quinoxalin-1-ylidene)carbohydrazides 4a-k; General Procedure Quinoxaline-2,3-dicarbonitrile (2; 0.63 g, 3.5 mmol) was dissolved by heating in anhydrous MeOH (30 mL) and the corresponding acid hydrazide (3.5 mmol) and NaOMe (0.35 mL, 1 N solution in MeOH) were added. The resulting mixture was refluxed with stirring for 4-6 h. After cooling, the precipitate formed was collected by filtration and washed with MeOH (5 mL). Recrystallization from MeOH, EtOH, or DMF afforded 4a-k. O. V. Hordiyenko et al. PAPER Synthesis 2013, 45, 3375-3382
PAPER
5H