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Thio radical-induced denitrogenative annulation of 1-azido-2-isocyanoarenes to construct 2-thiolated benzimidazoles

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Abstract

A method for the synthesis of 2-thiolated benzimidazoles is described starting from thiols and 1-azido-2-isocyanoarenes. The isocyano group works as an acceptor of various thio radicals, followed by denitrogenative annulation of the resulting imidoyl radical intermediates to the azido group, with nitrogen loss as the only process involving high bond-forming efficiency. The one-pot method for the synthesis of these products with high functional group tolerance in the benzimidazole-based ring is not available in previous literature.

Graphical abstract: Thio radical-induced denitrogenative annulation of 1-azido-2-isocyanoarenes to construct 2-thiolated benzimidazoles

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Publication details

The article was received on 07 Oct 2019, accepted on 22 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB02165E
Org. Biomol. Chem., 2019, Advance Article

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    Thio radical-induced denitrogenative annulation of 1-azido-2-isocyanoarenes to construct 2-thiolated benzimidazoles

    D. Li and J. Lei, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB02165E

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