Lewis Acids-catalyzed electrophilic substitution of indole with carbonyl compounds

ORGN 514

Bimal K. Banik, banik@panam.edu and Calista Aguilar. Department of Chemistry, The University of Texas-Pan American, 1201 W. University Drive, Edinburg, TX 78541
Bis(indolyl)alkanes and their derivatives are very attractive compounds because of their medicinal properties. The reaction of indoles with carbonyl compounds in some cases produce bis-indole derivatives. Excess protic acids and Lewis acid are known to promote this reaction. In recent years, many other syntheses of bis-indoles derivatives are prepared under catalytic conditions. We have reported the use of bismuth nitrate in several organic transformations. In particular, recently we have demonstrated a facile method for the synthesis of substituted pyrroles and indolinones. During the course of this study, we develop a new pathway for the synthesis of bis(indolyl)alkanes through bismuth nitrate-catalyzed reaction. The reaction of various indoles with carbonyl compounds in the presence of catalytic amounts of bismuth nitrate in ethanol produced bisindoles along with some unidentified products. This reaction has been performed under different conditions: without solvent and under microwave irradiation.