Tetrahedron

Synthesis of fused bicyclic glutarimides

MY Chang, CY Chen, ST Chen, NC Chang

Index: Chang, Meng-Yang; Chen, Chung-Yi; Chen, Shui-Tein; Chang, Nein-Chen Tetrahedron, 2003 , vol. 59, # 38 p. 7547 - 7553

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Citation Number: 12

Abstract

We describe an efficient route towards the synthesis of fused bicyclic glutarimides using facile [3+ 3] reaction of α-sulfonylacetamides with different α, β-unsaturated esters as the key step. Intramolecular cyclization of 4-substituted 3-sulfonylglutarimide to form 5, 6-, 6, 6-or 6, 7-fused bicyclic glutarimides was accomplished via alkylation, oxidative cyclization or ring- closing metathesis in modest yield.