Thermal fragmentation and rearrangement of some N-phenylbenzamide oxime dervatives II. Synthesis of benzimidazoles☆

Add time:09/02/2019    Source:sciencedirect.com

Thermolysis of N-phenylbenzamide oximes I, II and III (R = Cl, NO2 and OCH3) under nitrogen gives rise to benzimidazoles as the major products (45–52%), in addition to benzonitrile, arylamines, benzoic acid, phenols, benzanilides, 2-phenyl benzoxazoles and carbazoles. In the presence of naphthalene, I gave α- and β-naphthols beside the previous products. Also heating of I under reflux boiling tetralin lead to the formation of 1-hydroxytetralin, α-tetralone and 1,1′-bitetralyl as the major products. The isolated products have been interpreted in the terms of a free radical mechanism involving the homolysis of N–O and/or C–N bonds.

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