Synthesis of Trifluoromethyl‐Containing Polysubstituted Aromatic Compounds by Diels–Alder Reaction of Ethyl 3‐Benz­amido‐2‐oxo‐6‐(trifluoromethyl)‐2H‐pyran‐5‐carboxylate. Issue 11 (27th February 2015)

• Record Type: Journal Article
• Authors: Kondratov, Ivan S.; Tolmachova, Nataliya A.; Dolovanyuk, Violetta G.; Gerus, Igor I.; Daniliuc, Constantin‐Gabriel; Haufe, Günter
• Is Part Of: European journal of organic chemistry. Issue 11(2015)
• Page Start: 2482
• Page End: 2491
• Publication Date: 2015-02-27
• Subjects: Synthetic methods -- Alkenes -- Alkynes -- Cycloaddition -- Carbocycles -- Amino acids -- Fluorine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500032
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Diels–Alder reactions of ethyl 3‐benzamido‐2‐oxo‐6‐(trifluoromethyl)‐2 H ‐pyran‐5‐carboxylate (1a ) with electronically different dienophiles, including cyclic enol ethers, cycloalkenes, α, β‐unsaturated ketones, and terminal acetylenes, are useful for the efficient and selective three‐step preparation of trifluoromethyl‐containing aromatic compounds such as 3‐aminobenzoic acid derivatives. We presume that the presence of the trifluoromethyl group is the main factor in determining the regioselectivity of the initial cycloaddition. Abstract : Reactions of ethyl 3‐benzamido‐2‐oxo‐6‐(trifluoromethyl)‐2 H ‐pyran‐5‐carboxylate with cyclic alkenes and terminal acetylenes are useful for the efficient and selective preparation of trifluoromethyl‐containing polyfunctionalised aromatic amino acid derivatives.