Theses and Dissertations - UTB/UTPA
Date of Award
8-2012
Document Type
Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
Dr. Bimal K. Banik
Second Advisor
Dr. Elamin E. Ibrahim
Third Advisor
Dr. John R. Villareal
Abstract
This study presents the synthesis and structure of newly discovered β-lactams and the mechanism of their synthesis via the Staudinger reaction. β-lactams known as 2-azetidinones, are four membered cyclic amides that have been extensively used and recognized as the central motif of the β-lactam antibiotics, the most widely employed family of antimicrobial agent to date. The Staudinger reaction involves the cycloaddition between an acid chloride with an imine, in presence of a tertiary base. The possibility of cooperative effects from two therapeutic functionalities in drug molecules, has prompted interest in the synthesis of Bis-β-lactams. The synthesis of 2 novel Bis-β-lactams was achieved through a series of 4 reactions: nitration, catalytic transfer hydrogenation (amination), preparation of Schiff base or imine, and Bis-β-lactam preparation. Two major products were characterized and these novel Bis-β-lactams were confirmed by both infrared and nuclear magnetic resonance spectroscopy as well as melting point.
Granting Institution
University of Texas-Pan American
Comments
Copyright 2012 Jocabed Marquez. All Rights Reserved.
https://www.proquest.com/dissertations-theses/synthesis-novel-bis-β-lactams/docview/1238205166/se-2