High-Yielding Synthesis of 3-Alkoxycarbonyl- and 3-Carboxamido-3-tropene Derivatives in Homogeneous Carbonylation Reactions of 3-Iodo-2-tropene

Laszlo      Horvath; Zoltan      Berente; Laszlo      Kollar

doi:10.2174/1570178053202856

Abstract

3-Iodo-2-tropene, synthesized from the corresponding ketone (tropinone) via its hydrazone, was carbonylated in palladium-catalyzed alkoxy- and aminocarbonylation reactions. The new synthetic approach provided the corresponding 3-carboxylic acid derivatives of pharmacological importance in chemospecific reactions and isolated in up to 87 % yields.

Keywords: tropane-skeleton, palladium, aminocarbonylation, alkoxycarbonylation, homogeneous catalysis

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Letters in Organic Chemistry

Title: High-Yielding Synthesis of 3-Alkoxycarbonyl- and 3-Carboxamido-3-tropene Derivatives in Homogeneous Carbonylation Reactions of 3-Iodo-2-tropene

Volume: 2 Issue: 2

Author(s): Laszlo Horvath, Zoltan Berente and Laszlo Kollar

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Keywords: tropane-skeleton, palladium, aminocarbonylation, alkoxycarbonylation, homogeneous catalysis

Abstract: 3-Iodo-2-tropene, synthesized from the corresponding ketone (tropinone) via its hydrazone, was carbonylated in palladium-catalyzed alkoxy- and aminocarbonylation reactions. The new synthetic approach provided the corresponding 3-carboxylic acid derivatives of pharmacological importance in chemospecific reactions and isolated in up to 87 % yields.

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Horvath Laszlo, Berente Zoltan and Kollar Laszlo, High-Yielding Synthesis of 3-Alkoxycarbonyl- and 3-Carboxamido-3-tropene Derivatives in Homogeneous Carbonylation Reactions of 3-Iodo-2-tropene, Letters in Organic Chemistry 2005; 2 (2) . https://dx.doi.org/10.2174/1570178053202856