Organic letters

Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines

B Janza, A Studer

Index: Janza, Birgit; Studer, Armido Organic Letters, 2006 , vol. 8, # 9 p. 1875 - 1878

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Citation Number: 70

Abstract

An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R1, oxidation to dihydro-1 H-cyclopenta [b] quinolines (for R1= aryl) or tautomerization to tetrahydro-1 H- cyclopenta [b] quinolines (for R1= CO2Me, CN) occurs. The heterocycles are obtained in ...

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