Three-Component Approach to Pyridine-Stabilized Ketenimines for the Synthesis of Diverse Heterocycles
Three-Component Approach to Pyridine-Stabilized Ketenimines for the Synthesis of Diverse Heterocycles
复制标题
DOI：
10.1021/acs.joc.9b01906
复制
发表时间：
2019-11-01
影响因子：
3.6
通讯作者：
Sharma, Indrajeet
中科院分区：
文献类型：
--
作者：
Massaro, Nicholas P.;Chatterji, Aayushi;Sharma, Indrajeet
酮胺胺是一种多功能合成中间体，能够在有机合成中进行新的转化。由于其固有的不稳定性和高反应性，它们通常是在原地产生的。在此，我们报道了吡啶稳定的酮亚胺两性离子盐，它是通过点击化学从容易获得的炔和磺酰叠氮化合物中制备的。为了证明它们对酮胺的同质反应性，这些盐被利用在级联序列中获得高功能化的喹啉，包括抗原虫剂的核心结构和有效的拓扑异构酶抑制剂Tas-103。
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.