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Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach.

ABSTRACT: (E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-n-butylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60-70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph(3)P=CHCO(2)Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.

SUBMITTER: Boeck F

PROVIDER: S-EPMC3510995 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach.

Boeck Florian F Blazejak Max M Anneser Markus R MR Hintermann Lukas L

Beilstein journal of organic chemistry 20120926

(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-n-butylphosphane (20 mol %) as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60-70 °C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph(3)P=CHCO(2)Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization. ...[more]

PMID: 23209495

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