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Diels–Alder Reaction of Ethyl 3‐Benzamido‐2‐oxo‐6‐(trifluoromethyl)‐2 H ‐pyran‐5‐carboxylate with Alkoxyalkenes as an Effective Approach to Trifluoromethyl‐Containing 3‐Aminobenzoic Acid Derivatives
Author(s) -
Kondratov Ivan S.,
Tolmachova Nataliya A.,
Dolovanyuk Violetta G.,
Gerus Igor I.,
Bergander Klaus,
Daniliuc ConstantinGabriel,
Haufe Günter
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301485
Subject(s) - trifluoromethyl , chemistry , pyran , ether , carboxylate , benzoates , medicinal chemistry , organic chemistry , diels–alder reaction , catalysis , alkyl
Abstract The Diels–Alder reactions of ethyl 3‐benzamido‐2‐oxo‐6‐(trifluoromethyl)‐2 H ‐pyran‐5‐carboxylate with ethyl vinyl ether, 2‐methoxypropene, and 1‐ethoxypropene were investigated. Under different reaction conditions, intermediate oxabicyclo[2.2.2]octenones, alkoxycyclohexadienes, or aromatic products [5‐benzamido‐2‐(trifluoromethyl)benzoates] were formed. The reaction is useful for the preparation of some hitherto unknown trifluoromethyl‐containing derivatives of 3‐aminobenzoic acid.