Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products

…, S Olguín-Uribe, A Millan-Ortíz, R Gamez-Montaño…

Index: Lopez-Valdez, German; Olguin-Uribe, Simon; Millan-Ortiz, Alejandra; Gamez-Montano, Rocio; Miranda, Luis D. Tetrahedron, 2011 , vol. 67, # 14 p. 2693 - 2701

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Citation Number: 16

Abstract

An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert- butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. ...