二膦催化的混合双迈克尔反应：吲哚啉、二氢吡啶并吡啶、苯并咪唑啉、四氢喹啉、四氢异喹啉、二氢苯并-1,4-恶嗪和二氢苯并-3,1-恶嗪的统一合成。
Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
出版信息
Org Lett. 2010 Mar 5;12(5):1084-7. doi: 10.1021/ol100078w.
Abstract
Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.
摘要
七种不同类型的苯并稠合 N-杂环化合物——吲哚啉、二氢吡啶、苯并咪唑啉、二氢苯并-3,1-恶嗪、苯并吗啡啉、四氢喹啉和四氢异喹啉——可以通过一步合成从简单的二亲核试剂和缺电子的炔烃中得到。这种强大的方法是通过使用二苯膦丙烷（DPPP）作为催化剂来实现的，在某些情况下，还使用乙酸和醋酸钠作为添加剂。在温和的无金属条件下，苯并稠合 N-杂环化合物以优异的收率被分离出来；它们无需进行水相处理即可得到纯化。
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