Tetrahedron p. 4109 - 4122 (1999)
Update date:2022-08-03
Topics: Radical cyclisation Heterocyclic compounds Organic chemistry Radical Imidazoles Cyclisation Benzimidazoles Synthesis
Aldabbagh, Fawaz
Bowman, W. Russell
New synthetic methodology has been developed for the synthesis of [1,2- a]fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(ω-alkyl) radicals are generated using Bu3SnH from N-(ω-phenylselanyl)alkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used at the leaving groups in the homolytic substitutions.
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