Ring opening reactions of quinoline substituted epoxides
AN Boa, S Clark, PR Hirst, R Westwood
Index: Boa, Andrew N.; Clark, Stephen; Hirst, Paul R.; Westwood, Robert Tetrahedron Letters, 2003 , vol. 44, # 52 p. 9299 - 9302
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Citation Number: 10
Abstract
6-Oxiranyl-and 3-oxiranyl-2-phenylquinoline-4-carboxylic acid diisopropylamides react with secondary amines and lithium amides to give (aminohydroxyethyl) quinolines but with opposite regioselectivities. Upon epoxidation of 3-formylquinoline 2 a∼ 5: 1 mixture of atropisomers is formed. This ratio is maintained upon epoxide ring-opening with amines in ethanol at reflux, but with lithium amides at room temperature a 1.3: 1 ratio of isomers is ...
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