Fi. Guseinov et al., REACTION OF ALPHA-HALO-BETA-OXOALDEHYDES AND ALPHA,ALPHA-DIHALO-BETA-OXOALDEHYDES WITH O-PHENYLENEDIAMINE AND M-PHENYLENEDIAMINE, Russian chemical bulletin, 47(3), 1998, pp. 459-461
alpha-Halo-beta-oxoaldehydes react with o- and m-phenylenediamines to
give alpha-halo-beta-oxoenamines. In the case of o-phenylenediamine, t
he initially formed monoenamine undergoes concurrent intramolecular cy
clization to give benzimidazole and a halocarbonyl compound. alpha,alp
ha-Dihalo-beta-oxoaldehydes react with o- and m-phenylenediamines acco
rding to the haloformic decomposition scheme involving formylation of
amino groups.