Tandem furo [3, 4-b] pyridine formation—Diels–Alder reaction: an approach to the synthesis of nitrogen containing heterocyclic analogues of 1-arylnaphthalene …

GP Jana, BK Ghorai

Index: Jana, Gouranga P.; Ghorai, Binay K. Tetrahedron, 2007 , vol. 63, # 48 p. 12015 - 12025

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Citation Number: 18

Abstract

The coupling of Fischer carbene complexes with 2-alkynyl-3-pyridine carbonyl derivatives has been examined. The reaction affords furo [3, 4-b] pyridine as transient intermediates; the latter undergo [4+ 2] cycloaddition with an electron-deficient dienophile. Acid/base-induced ring opening of the exo-cycloadducts followed by aromatization give substituted quinolines related to heterocyclic analogues of 1-arylnaphthalene lignans. An intramolecular variant ...