Tetrahedron letters

Synthesis of diastereomeric 2, 4-disubstituted pyrano [2, 3-b] quinolines from 3-formyl-2-quinolones through O–C bond formation via intramolecular electrophilic …

MK Singh, A Chandra, B Singh, RM Singh

Index: Singh, Mrityunjay K.; Chandra, Atish; Singh, Bhawana; Singh, Radhey M. Tetrahedron Letters, 2007 , vol. 48, # 34 p. 5987 - 5990

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Citation Number: 53

Abstract

A number of 3-homoallyl-2-quinolones have been synthesized from 3-formyl-2-quinolones by reaction with allylindium bromide in aqueous DMF. Intramolecular electrophilic cyclization of these quinolones with iodine afforded either exclusively, or predominantly, racemic cis-diastereoisomers. Nucleophilic substitution reactions at the iodomethyl group afforded a mixture of tetracyclic products and unreacted racemic trans-diastereoisomer.