The Journal of organic chemistry

A sequential Pummerer-Diels-Alder route for the generation and trapping of furo [3, 4-c] pyridines: Synthesis of heterocyclic analogues of 1-arylnaphthalene lignans

TK Sarkar, N Panda, S Basak

Index: Sarkar, Tarun K.; Panda, Niranjan; Basak, Sankar Journal of Organic Chemistry, 2003 , vol. 68, # 18 p. 6919 - 6927

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Citation Number: 19

Abstract

The Pummerer reaction of an o-benzoyl-substituted pyridylmethyl sulfoxide generates an α- thiocarbocation, the interception of which by a neighboring keto functionality produces an α- thio-substituted furo [3, 4-c] pyridine as transient intermediate; the latter undergoes a Diels- Alder cycloaddition with an added dienophile. Base-induced ring opening of the cycloadduct followed by aromatization gives an isoquinoline derivative that may be looked upon as a ...