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

Florian Boeck; Max Blazejak; Markus R. Anneser; Lukas Hintermann

doi:10.3762/bjoc.8.186

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

Florian Boeck, Max Blazejak, Markus R. Anneser, Lukas Hintermann

Associate Professorship of Organic Chemistry

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (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 ₃P=CHCO ₂Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.

Original language	English
Pages (from-to)	1630-1636
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	8
DOIs	https://doi.org/10.3762/bjoc.8.186
State	Published - 26 Sep 2012

Keywords

Catalysis
Coumarins
Heterocycles
Mechanisms
Organocatalysis
Phosphanes

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10.3762/bjoc.8.186

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abstract = "(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (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 3P=CHCO 2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.",

keywords = "Catalysis, Coumarins, Heterocycles, Mechanisms, Organocatalysis, Phosphanes",

author = "Florian Boeck and Max Blazejak and Anneser, {Markus R.} and Lukas Hintermann",

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T1 - Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions

T2 - A nucleophilic organocatalysis approach

AU - Boeck, Florian

AU - Blazejak, Max

AU - Anneser, Markus R.

AU - Hintermann, Lukas

PY - 2012/9/26

Y1 - 2012/9/26

N2 - (E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (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 3P=CHCO 2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.

AB - (E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 °C. We find that the use of tri-nbutylphosphane (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 3P=CHCO 2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.

KW - Catalysis

KW - Coumarins

KW - Heterocycles

KW - Mechanisms

KW - Organocatalysis

KW - Phosphanes

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DO - 10.3762/bjoc.8.186

M3 - Article

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SN - 1860-5397

VL - 8

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EP - 1636

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

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