4-Chloro-2-fluoro-5-nitrobenzoic acid is a commercially
available
multireactive building block that can serve as a starting material
in heterocyclic oriented synthesis (HOS) leading to various condensed
nitrogenous cycles. This work describes its ability for the preparation
of substituted nitrogenous heterocycles having 5–7-membered
cycles via polymer-supported <i>o</i>-phenylendiamines.
Immobilization of this compound on Rink resin followed by further
chlorine substitution, reduction of a nitro group and appropriate
cyclization afforded benzimidazoles, benzotriazoles, quinoxalinones,
benzodiazepinediones and succinimides. The method developed is suitable
for the synthesis of diverse libraries including the mentioned types
of heterocycles, which have significant importance in current drug
discovery. In this paper, we also report limitation of these method
and unsuccessful attempt to prepare an 8-membered benzodiazocine cycle