A New Approach to the Synthesis of 1-Arylbenzimidazole-2-thiones from Nitroarenes and Anilines through Halogen-Free Substitution of Hydrogen via Iminophosphorane Intermediates

Abstract

2-(Arylamino)phenyliminophosphoranes, formed directly from 2-nitrosodiarylamines, undergo a high-yielding cyclocondensation with CS₂, providing a variety of 1-arylbenzimidazole-2-thiones. The reaction concludes a new synthetic route leading to the title compounds from simple nitroarenes and arylamines. The protocol is superior to common methods that use N-arylarylenediamines because it omits the S_NAr substitution of halogen atoms in ortho-halonitroarenes, as well as reduction processes required for the synthesis of the intermediate diamines.

Key words

annulation - nitrogen heterocycles - cyclization - nitroso compounds - fused-ring systems

• References

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