ORGN 745 |
| Bismuth salts have become very popular in the synthesis of several organic compounds. There are a number of advantages of using bismuth salts. For example, most of them are commercially available, non-toxic and very economical. 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. During the course of this study and in continuation of our endeavor for the synthesis and biological evaluation of novel beta-lactams, we develop a new pathway for the synthesis of beta-lactams that have a pyrrole ring at the C-3 position of the azetidinone ring in excellent yield. The reaction of 3-cis and trans amino beta-lactams with commercially available acetonyl acetone in the presence of catalytic amounts of bismuth nitrate in organic solvents has produced beta-lactams substituted with a pyrrole ring at the C-3 position. Although the chemistry of beta-lactams is extremely rich, methods for the preparation of pyrrole substituted azetidinones is not known. A few other acids including bismuth-derived reagents have also been tested. It has been found that the success of this reaction depends on the concentration of the catalyst loading and nature of the solvent. |
|
Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |