Three-Component Approach to Pyridine-Stabilized Ketenimines for the Synthesis of Diverse Heterocycles
Nicholas P Massaro1, Aayushi Chatterji1, Indrajeet Sharma1
1Department of Chemistry and Biochemistry, and Institute of Natural Products Applications and Research Technologies , University of Oklahoma , 101 Stephenson Parkway , Norman , Oklahoma 73019 , United States.
Abstract:
Ketenimines are versatile synthetic intermediates capable of performing novel transformations in organic synthesis. They are normally generated in situ due to their inherent instability and high level of reactivity. Herein, we report pyridine-stabilized ketenimine zwitterionic salts, which are prepared through click chemistry from readily accessible alkynes and sulfonyl azides. To demonstrate their synonymous reactivity to ketenimines, these salts have been utilized in a cascade sequence to access highly functionalized quinolines including the core structures of an antiprotozoal agent and the potent topoisomerase inhibitor Tas-103.
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