Synlett

Synthesis of Isoquinoline Alkaloids via Oxidative Amidation-Bischler-Napieralski Reaction

R Shankar, SS More, MV Madhubabu, N Vembu…

Index: Shankar; More, Satish S.; Madhubabu; Vembu; Syam Kumar Synlett, 2012 , vol. 23, # 7 p. 1013 - 1020

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Citation Number: 11

Abstract

Abstract A straightforward synthesis of α-keto amides by coupling primary amines with aryl dibromoethanones under oxidative amidation conditions has been developed. The α-keto amides were then subjected to heterocyclodehydration reaction under Bischler-Napieralski conditions followed by aromatization with DBU provided 1-benzoyl isoquinolines in a two- stage process. Utilizing this methodology, isoquinoline alkaloids such as thalmicrinone, ...