Unusual C-6 lithiation of 2-chloropyridine-mediated by BuLi-Me2N(CH2)2OLi.: New access to 6-functional-2-chloropyridines and chloro-bis-heterocycles

被引：79

作者：

Choppin, S ^{[1
]}

Gros, P ^{[1
]}

Fort, Y ^{[1
]}

机构：

[1] Univ Nancy 1, Fac Sci, CNRS, UMR UHP 7565, F-54506 Vandoeuvre Nancy, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 06期

关键词：

D O I：

10.1021/ol005538o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 5-chloropyridine with alkylithium generally results in nucleophilic addition leading to the loss of chlorine atom while exclusive directed ortho metalation is obtained using LDA. Herein it is shown that the BuLi-Me2N(CH2)(2)OLi (BuLi-LiDMAE) superbase promotes an unprecedented regioselective C-6 lithiation. The method was successfully applied to the preparation of potentially useful chlorinated pyridinic and bis-heterocyclic synthons.

引用

页码：803 / 805

页数：3

共 14 条

[1]

[Anonymous], 1999, J CHEM EDUC

[2]

FIELD JS, 1993, S AFR J CHEM-S-AFR T, V46, P70

[3] REGIOSELECTIVE ORTHO LITHIATION OF HALOPYRIDINES [J].

GRIBBLE, GW ;

SAULNIER, MG .

TETRAHEDRON LETTERS, 1980, 21 (43) :4137-4140

[4]

GROS P, 1995, TETRAHEDRON LETT, V36, P4791

[5] Regio selective functionalisation of 2-(diphenylphosphino)-pyridine:: direct lithiation at the pyridine C-6 position [J].

Gros, P ;

Ben Younès-Millot, C ;

Fort, Y .

TETRAHEDRON LETTERS, 2000, 41 (03) :303-306

[6]

GROS P, 1997, J CHEM SOC P1, V24, P3597

[7]

GROS P, 1997, J CHEM SOC P1, V20, P3071

[8]

Gros P., 1998, J CHEM SOC P1, V10, P1685

[9]

MARSAIS F, 1983, TETRAHEDRON, V39, P2009, DOI 10.1016/S0040-4020(01)91919-2

[10] NEW CONTRACTIVE COUPLING PROCEDURE - CONVENIENT PHOSPHORUS EXPULSION REACTION [J].

NEWKOME, GR ;

HAGER, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (17) :5567-5568

← 1 2 →