Bu 3 SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

F Aldabbagh, WR Bowman, E Mann, AMZ Slawin

Index: Aldabbagh, Fawaz; Russell Bowman; Mann, Emma; Slawin, Alexandra M.Z. Tetrahedron, 1999 , vol. 55, # 26 p. 8111 - 8128

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Citation Number: 69

Abstract

A new protocol using radical cyclisation has been developed for the synthesis of [1, 2-c]- fused imidazoles and [1, 2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N-(ω-bromoalkyl) or N-[ω-(phenylselanyl) alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisation onto the azole rings followed by oxidative re-aromatisation.