Synthesis of heteroarenes using cascade radical cyclisation via iminyl radicals

WR Bowman, MO Cloonan, AJ Fletcher…

Index: Bowman, W. Russell; Cloonan, Martin O.; Fletcher, Anthony J.; Stein, Tobias Organic and Biomolecular Chemistry, 2005 , vol. 3, # 8 p. 1460 - 1467

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Citation Number: 57

Abstract

Cascade radical cyclisation involving homolytic aromatic substitution has been used to synthesise new tetracycles. Treatment of vinyl iodide radical precursors with Me3Sn˙ radicals (from hexamethylditin) yielded intermediate vinyl radicals which undergo 5-exo cyclisation onto suitably placed nitrile groups to yield intermediate iminyl radicals. The iminyl radicals undergo aromatic homolytic substitution via 6-endo cyclisation (or 5-exo ...