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Reactions of 3‐oxo‐2,3‐dihydrobenzofuran with alkyl 2‐cyano‐3‐alkoxypropenoate and alkyl 2‐alkoxycarbonyl‐3‐alkoxypropenoate. Synthesis of pyran derivatives
Author(s) -
Mérour J. Y.,
Cossais F.
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280813
Subject(s) - chemistry , pyran , alkyl , benzofuran , medicinal chemistry , organic chemistry , stereochemistry
3‐Oxo‐2,3‐dihydrobenzofuran reacted with ethyl 2‐cyano‐3‐ethoxypropenoate, methyl 2‐cyano‐3‐methoxy‐propenoate affording compounds 3 (2‐(2‐cyano‐2‐alkoxycarbonylvinyl)‐3‐hydroxybenzofuran) obtained as a mixture of Z + E isomers. Methyl 2‐methoxycarbonyl‐3‐methoxypropenoate gave compound 4 . Malonic compounds added on 2‐dimethylaminomethylene‐3‐oxo‐2,3‐dihydrobenzofuran 6 for giving compound 3 or 2‐oxo‐3‐methoxycarbonyl‐2 H ‐pyrano[3,2‐ b ]benzofuran 8 . Compound 8 was also obtained by heating compound 4 in xylene.