Tetrahedron

Radical annulations with nitriles: Novel cascade reactions of cyano-substituted alkyl and sulfanyl radicals with isonitriles

CM Camaggi, R Leardini, D Nanni, G Zanardi

Index: Camaggi, Carlo Maurizio; Leardini, Rino; Nanni, Daniele; Zanardi, Giuseppe Tetrahedron, 1998 , vol. 54, # 21 p. 5587 - 5598

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Citation Number: 47

Abstract

New radical annulation reactions are described involving addition of cyano-substituted alkyl and sulfanyl radicals to aromatic isonitriles. The tandem cyclisation of the resulting imidoyl radicals onto the cyano group affords cyclopenta-and thienoquinoxalines, respectively. The intervention of the isonitriles in the aromatisation process of the cyclohexadienyl radicals is discussed, as well as the regiochemistry of the cyclisation of the iminyl radicals obtained ...