通过 Mg 和 Zn 有机金属中间体对吡啶和生物碱进行选择性和多功能化。

Selective and multiple functionalization of pyridines and alkaloids via Mg- and Zn-organometallic intermediates.

机构信息

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany.

出版信息

Org Lett. 2011 May 6;13(9):2306-9. doi: 10.1021/ol200563j. Epub 2011 Apr 4.

DOI:10.1021/ol200563j

Abstract

Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF(3)·OEt(2). A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of TMP bases in the presence or absence of BF(3)·OEt(2).

摘要

奎宁、尼古丁和相关的富电子氨基取代吡啶很容易在 LiCl 增溶的 TMP（2,2,6,6-四甲基哌啶）碱和 BF(3)·OEt(2)存在下进行金属化。通过在存在或不存在 BF(3)·OEt(2)的情况下适当组合 TMP 碱，可以实现吡啶环的所有五个位置的完全吡啶官能化。