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http://ir.ncue.edu.tw/ir/handle/987654321/14947
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| Title: | Synthesis of Cyclo-2,2' :4',4'':2'',2''':4''',4'''':2'''',2'''':4''''',4-sexipyridine |
| Authors: | Kelly, T. R.;Lee, Yean-Jang;Mears, R. J. |
| Contributors: | 化學系 |
| Date: | 1997-05
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| Issue Date: | 2012-12-10T02:51:25Z
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| Publisher: | American Chemical Society |
| Abstract: | 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. |
| Relation: | J. Org. Chem., 62(9): 2774-2781 |
| Appears in Collections: | [化學系] 期刊論文
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