Synthesis and structure elucidation of pyrimidobenzimidazoles and fused derivatives II [1]. Dodecahydrobenzimidazo-[2,1-b]quinazolines and decahydrobenzimidazo-[2,1-b]benzo[h]quinazolines [2]

Abstract

The cyclization reactions of trans-3a-hexahydro-2-benzimidazolamine with 2-alkylidene-and 2-benzylidenecyclohexanones and α-tetralones, respectively, yield mixtures of two isomeric condensates each. Thorough high resolution NMR analyses (1H and 13C NMR, HH-COSY, gs-HSQC, gs-HMBC, 1D TOCSY, and 1D NOE difference spectra) revealed that the corresponding isomers are in all cases linearly fused diastereomeric 12α-and 12β-substituted trans-6aα-dodecahydrobenzimidazo[2,1-b]quinazolines and 7α-substituted trans-8aβ-and trans-8aα-decahydrobenzimidazo[2,1-b]benzo[h]quinazolines, respectively. The formation of corresponding angularly fused regioisomers was not observed so far. The stereochemistry and the tautomerism of some bases and their hydrochlorides as well as the regiospecific course of the cyclization reactions are discussed. Biological tests showed that the novel compounds don't exert remarkable antibacterial and antimycotic effects.