Bismuth nitrate-catalyzed synthesis of pyrroles

ORGN 102

Bimal K. Banik, banik@panam.edu1, Indrani Banik2, Jacobed Marquez1, and Clarissa Alvarez1. (1) Department of Chemistry, The University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, (2) Department of Molecular Pathology, The University of Texas M. D. Anderson Cancer Center, 1515 Holcombe Blvd., Houston, TX 77030

In our earlier paper, we have performed a structure-activity relationship study of various polyaromatic compounds prepared from their corresponding amines toward the development of novel anticancer agents.  Based on the promising biological activity of these compounds, we became interested in the synthesis of pyrroles bound to the polyaromatic amines.  It has been realized that our own work on bismuth nitrate-catalyzed organic transformations could be very fruitful for the facile synthesis of pyrroles under very mild conditions.  In our procedure, the starting materials (amines and 2, 5-diketone) are mixed with bismuth nitrate (5 mol%) in the presence of dichloromethane and the solution is kept at room temperature.  Notably, this method has been proved to be highly effective for the synthesis of pyrroles with several less nucleophilic polyaromatic amines.