Bicyclic lactams from imidosulfone cyclizations: Functionalization and applications to pyrrole synthesis

ORGN 165

Aravamudan S. Gopalan, agopalan@nmsu.edu, Nora M. Hernandez, nomorale@nmsu.edu, Frank A. Sanchez, francisschem@hotmail.com, and Hollie K. Jacobs. Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003-8001

Recent work in our laboratory has shown that imidosulfones of the type I undergo efficient cyclization reactions with base to give bicyclic lactams of the type II. These lactams are potential intermediates for the preparation of interesting indolizidine and quinolizidine alkaloids. Hence, we have examined the reactivity and further functionalization of lactams II. Reaction of II (n=1, m=1,2) with carbon nucleophiles such as lithiomethylphenylsulfone leads to nucleophilic attack at the amide carbonyl to give the corresponding adducts. These intermediates undergo acid catalyzed elimination to yield pyrroles of the type III. However, the corresponding chemistry of cyclic lactam II (n=2) is quite different. We will also discuss the reaction of II with heteroatom nucleophiles such as thiophenol and others. The interesting reduction chemistry of lactams II will also be presented.