An annulation method for the synthesis of alkyl-substituted 6-carbomethoxy-2-pyridones

被引：10
|
作者：
Zhang, Yu [1 ]
Loertscher, Brad M. [1 ]
Castle, Steven L. [1 ]
机构：
[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA
来源：
TETRAHEDRON | 2009年 / 65卷 / 33期
基金：
美国国家科学基金会;
关键词：
Lyconadin A; Pyridone; Mannich reaction; Reformatsky reaction; Desulfurization; ONE-POT SYNTHESIS; REFORMATSKY REACTION; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; 2-PYRIDONES; PYRIDIN-2(1H)-ONES; ANALOG; (+)-LYCONADIN-A; CYCLOADDITION; LIGANDS;
D O I：
10.1016/j.tet.2009.06.006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A protocol for the synthesis of 5-alkyl and 3,5-dialkyl-6-carbomethoxy-2-pyridones was devised. Key steps include a Mannich reaction, acylation of a tosylamine, and a PPh3/TiCl4-promoted intramolecular Reformatsky-type reaction with a thioester as the electrophile. The latter process typically afforded a vinylogous thiocarbamate via elimination of water rather than the Dieckmann-type product which would have resulted from elimination of the thiol. However, the Dieckmann-type ketone product was obtained in one instance. Subsequent elimination of the tosyl group and desulfurization completed the pyridone synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6584 / 6590
页数：7
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