Tetrahedron

Studies on the regioselectivity of intermolecular diels-alder cycloadditions of 1-methylpyrano [3, 4-b] indol-3-one and the N-acetylated derivative

HN de Carvalho, GI Dmitrienko, KE Nielson

Index: Carvalho, Helena Nandin de; Dmitrienko, Gary I.; Nielson, Kent E. Tetrahedron, 1990 , vol. 46, # 16 p. 5523 - 5532

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Citation Number: 3

Abstract

Diels-Alder reactions of the 1-methylpyrano [3, 4-b] indol-3-one 1a with less than two equivalents of methyl acrylate and methyl vinyl ketone occur with complete regioselectivity to yield the corresponding 3-substituted 1-methyl-1, 2-dihydrocarbazole derivatives 3. Cycloadditions of the N-acetyl-1-methylpyrano [3, 4-b] indol-3-one 1b with the same dienophiles proceed at a much slower rate to yield adducts incorporating two molecules of ...