Bismuth compounds in organic synthesis: Bismuth bromide catalyzed synthesis of substituted quinolines

ORGN 473

Ram S. Mohan, rmohan@iwu.edu, Jamie L. Rogers, and Herbie Yung, hyung@iwu.edu. Laboratory for Environmentally Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, 201 East Beecher Street, Bloomington, IL 61701
The quinoline skeleton is found in a wide range of natural products and hence considerable attention has been given to methods for their synthesis. A variety of hexahydrofuro[3,2,c]quinolines are obtained in moderate yields via a bismuth bromide catalyzed coupling between substituted anilines and two equivalents of dihydrofuran or dihydropyran. The product is obtained as a mixture of endo and exo isomers, with the endo being the major product. Bismuth compounds are attractive because of their remarkably low toxicity, low cost and ease of handling. The results of this study will be presented.