外环烯丙型酰胺和氨基甲酸酯的氮杂-和碳杂-[3 + 3]环合反应。四氢吲哚嗪的合成及六氢喹啉的意外生成。
Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.
作者信息
Ghosh Sunil K, Buchanan Grant S, Long Quincy A, Wei Yonggang, Al-Rashid Ziyad F, Sklenicka Heather M, Hsung Richard P
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, 777 Highland Avenue, Rennebohm Hall, University of Wisconsin Madison, WI 53705 USA.
出版信息
Tetrahedron. 2008 Jan 28;64(5):883-893. doi: 10.1016/j.tet.2007.09.089.
Abstract
[3 + 3] Annulations of exo-cyclic vinylogous amides and urethanes with vinyl iminium salts are described here. We observed an intriguing dichotomy in their reaction pathways. For pyrrolidine- and azepane-based vinylogous amides or urethanes, aza-[3 + 3] annulation would dominate to give tetrahydroindolizidines, whereas, unexpectedly, for piperidine-based vinylogous amides or urethanes, carbo-[3 + 3] annulation was the pathway, leading to hexahydroquinolines. The origin for such a contrast is likely associated with a switch in the initial reaction pathway between C-1,2-addition and C-1,4-addition.
摘要
本文描述了环外烯醇酰胺和氨基甲酸酯与乙烯基亚胺盐的[3 + 3]环化反应。我们观察到它们的反应途径存在有趣的二分法。对于基于吡咯烷和氮杂环庚烷的烯醇酰胺或氨基甲酸酯，氮杂-[3 + 3]环化反应占主导，生成四氢吲哚嗪，而出乎意料的是，对于基于哌啶的烯醇酰胺或氨基甲酸酯，碳-[3 + 3]环化反应是反应途径，生成六氢喹啉。这种差异的起源可能与C-1,2-加成和C-1,4-加成之间初始反应途径的转变有关。
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