Aa. Geies et al., SYNTHESIS OF NEW TRIAZOLOQUINOXALINES, PYRROLOQUINOXALINES, AND PYRIMIDOPYRROLOQUINOXALINES, Monatshefte fuer Chemie, 127(12), 1996, pp. 1263-1272
When 2-hydroxyquinoxaline-3-carboxamide (1) was reacted with POCl3 in
DMF, 2-chloro-3-dimethylaminomethylenecarboxamide (2) was obtained. Th
e chloro compound 2 was reacted with thiourea and hydrazine hydrate to
give the corresponding mercapto and hydrazino derivatives 3 and 8, re
spectively. On the other hand, 2-chloroquinoxaline-3-carbonitrile (13)
reacted with ethyl glycinate to the glycinate derivative 14 which was
cyclized to pyrroloquinoxaline 15 by heating with sodium ethoxide. Py
rimidopyrroloquinoxaline derivatives 16 and 17 were obtained via the r
eaction of 15 with formamide and phenyl isothiocyanate, respectively.