期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 8, 期 -, 页码 1630-1636出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.8.186
关键词
catalysis; coumarins; heterocycles; mechanisms; organocatalysis; phosphanes
资金
- Deutsche Forschungsgemeinschaft [SPP 1179]
(E)-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140-250 degrees 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 degrees C). Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph3P=CHCO2Me to (E)-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.
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