Article
Substituted 4-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic Esters by a Tandem Imine Addition-SNAr Reaction
Richard A. Bunce,
James E. Schammerhorn,
Jessica Sigle,
Corresponding Author
Richard A. Bunce
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078-3071
E-mail: [email protected]Search for more papers by this authorJames E. Schammerhorn
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078-3071
Search for more papers by this authorJessica Sigle
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078-3071
Search for more papers by this authorRichard A. Bunce,
James E. Schammerhorn,
Jessica Sigle,
Corresponding Author
Richard A. Bunce
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078-3071
E-mail: [email protected]Search for more papers by this authorJames E. Schammerhorn
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078-3071
Search for more papers by this authorJessica Sigle
Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma, 74078-3071
Search for more papers by this authorAbstract
A tandem imine addition-SNAr annulation reaction has been developed as a new approach to the synthesis of 4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic esters. A series of these structures has been generated by reacting selected imines with tert-butyl 2-fluoro-5-nitrobenzoylacetate. Structural variations in the final products are accomplished by changing the substituents on the imine and the alkyl group of the ester. The title compounds are isolated as their enols in 55–97% yield without the need for added base or catalysts. The synthesis of the starting materials as well as mechanistic studies and further synthetic conversions of the products are presented.
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