Zhang Xiaoxia, Yao Tuanli, Campo Marino A, Larock Richard C
Department of Chemistry, Iowa State University, Ames, Iowa 50011.
Tetrahedron. 2010 Feb 6;66(6):1177. doi: 10.1016/j.tet.2009.12.012.
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I(2), Br(2), PhSeBr and p-O(2)NC(6)H(4)SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)(2)-catalyzed ring closure of these same alkynylanilines.
通过N-(2-炔基)苯胺与ICl、I₂、Br₂、PhSeBr和对硝基苯磺酰氯进行6-内型亲电环化反应，可在温和的反应条件下轻松合成多种取代喹啉。在各种官能团存在的情况下，该反应能以中等至良好的产率得到含3-卤素、硒和硫的喹啉。通过这些相同的炔基苯胺在Hg(OTf)₂催化下闭环反应，已合成了在3-位带有氢原子的类似喹啉。
