National Changhua University of Education Institutional Repository : Item 987654321/14947
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题名: Synthesis of Cyclo-2,2' :4',4'':2'',2''':4''',4'''':2'''',2'''':4''''',4-sexipyridine
作者: Kelly, T. R.;Lee, Yean-Jang;Mears, R. J.
贡献者: 化學系
日期: 1997-05
上传时间: 2012-12-10T02:51:25Z
出版者: American Chemical Society
摘要: Preparation of the title compound (2) by use of Stille couplings and a Kröhnke pyridine synthesis is described. By application of the Stille coupling reaction, preparation and functionalization of quater- and quinquepyridines 26, 27, and 28 were achieved. Elaboration of quinquepyridine 27 to the pyridinium salt 30 bearing a protected enal allowed for the synthesis of 2 by a one-pot deprotection/Kröhnke reaction in nine steps from 4,4‘-bipyridine. Use of the Kröhnke pyridine synthesis has been applied to prepare sexipyridine dibromide 19, but attempts to induce a macrocyclization via metal-mediated (Pd/Ni/Cu) aryl−aryl coupling procedures proved unsuccessful. Acetylene-bridged sexipyridines 3a and 3b incorporating 2,2‘-bipyridine units proved to be inaccessible via sp−sp2 or sp−sp coupling protocols.
關聯: J. Org. Chem., 62(9): 2774-2781
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