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- W2083974913 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 the dienophile. In this case the regioselectivity appears to have been reversed in both steps of the Diels-Alder reaction since the bis-adducts obtained as major products have the substituents on the C2 and C2' carbon. The reaction of 1a with the symmetrical dienophile dimethylfumarate produces a mixture of the cis and trans 1-methyl-9H-1,2-dihydrocarbazole-2, 3-dicarboxylic acid dimethyl esters 16 and 17 in the ratio of 1 : 3.7 respectively." @default.
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- W2083974913 date "1990-01-01" @default.
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- W2083974913 title "Studies on the regioselectivity of intermolecular diels-alder cycloadditions of 1-methylpyrano[3,4-b]indol-3-one and the N-acetylated derivative" @default.
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- W2083974913 doi "https://doi.org/10.1016/s0040-4020(01)87750-4" @default.
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