Acid-promoted cyclization reactions of tetrahydroindolinones. model studies for possible application in a synthesis of selaginoidine

MD Rose, MP Cassidy, P Rashatasakhon…

Index: Rose, Mickea D.; Cassidy, Michael P.; Rashatasakhon, Paitoon; Padwa, Albert Journal of Organic Chemistry, 2007 , vol. 72, # 2 p. 538 - 549

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Citation Number: 19

Abstract

The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare ...