First regioselective C-2 lithiation of 3-and 4-chloropyridines

被引:2
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 Les Nancy, France
关键词
chloropyridines; lithiation; regioselectivity; complexation;
D O I
10.1002/1099-0690(200102)2001:3<603::AID-EJOC603>3.0.CO;2-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have shown that the BuLi/LiDMAE reagent promotes the clean and regioselective C2 lithiation of 3- and 4-chloropyridines, while other reagents such as LDA or BuLi/TMEDA lead to classical ortho lilhiation products or mixtures of regioisomers. The method was successfully applied to the preparation of various reactive 2,3- and 2,4-disubstituted pyridines.
引用
收藏
页码:603 / 606
页数:4
相关论文
共 50 条
  • [21] Remarkable effect of water in a regioselective lithiation of 5-(tert-butoxycarbonyl)-7-methoxy-1-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline
    Moro-oka, Y
    Iwakiri, S
    Fukuda, T
    Iwao, M
    [J]. TETRAHEDRON LETTERS, 2000, 41 (27) : 5225 - 5228
  • [22] First Palladium-Catalyzed Direct Regioselective C-5 (Het) Arylation of Mono- or Disubstituted Thiazolo[3,2-b][1,2,4]triazoles
    Le Meur, Mikael
    Bourg, Stephane
    Massip, Stephane
    Marchivie, Mathieu
    Jarry, Christian
    Guillaumet, Gerald
    Routier, Sylvain
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3704 - 3714
  • [23] A convenient K2CO3 catalysed regioselective synthesis for benzopyrano[4,3-c]pyrazoles in aqueous medium
    Kidwai, Mazaahir
    Priya
    Singhal, Kavita
    Rastogi, Shweta
    [J]. HETEROCYCLES, 2007, 71 (03) : 569 - 576
  • [24] Regioselective Exohedral Functionalization of La@C82 and its 1,2,3,4,5-Pentamethylcyclopentadiene and Adamantylidene Adducts
    Maeda, Yutaka
    Sato, Satoru
    Inada, Koji
    Nikawa, Hidefumi
    Yamada, Michio
    Mizorogi, Naomi
    Hasegawa, Tadashi
    Tsuchiya, Takahiro
    Akasaka, Takeshi
    Kato, Tatsuhisa
    Slanina, Zdenek
    Nagase, Shigeru
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (07) : 2193 - 2197
  • [25] Li3V2(PO4)3 cathode material synthesized by chemical reduction and lithiation method
    Zheng, Jun-Chao
    Li, Xin-Hai
    Wang, Zhi-Xing
    Guo, Hua-Jun
    Hu, Qi-Yang
    Peng, Wen-Jie
    [J]. JOURNAL OF POWER SOURCES, 2009, 189 (01) : 476 - 479
  • [26] Efficient Synthesis and First Regioselective C-3 Direct Arylation of Imidazo[1,2-b]pyrazoles
    Grosse, Sandrine
    Pillard, Christelle
    Massip, Stephane
    Leger, Jean Michel
    Jarry, Christian
    Bourg, Stephane
    Bernard, Philippe
    Guillaumet, Gerald
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (47) : 14943 - 14947
  • [27] Regioselective annelation of 3-(prop-2-ynylsulfanyl)-1,2,4-benzotriazine to thiazolo[2,3-c][1,2,4]benzotriazine
    Heravi, MM
    Aghapoor, K
    Nooshabadi, MA
    Mojtahedi, MM
    [J]. MONATSHEFTE FUR CHEMIE, 1997, 128 (11): : 1143 - 1147
  • [28] Regioselective synthesis of 6-substituted-2-amino-5-bromo-4(3H)-pyrimidinones and evaluation of their antiviral activity
    Singh, Kamaljit
    Singh, Kawaljit
    Balzarini, Jan
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 67 : 428 - 433
  • [29] Rhodium-Catalyzed Regioselective C-O and C-C Bonds Formation of 3-Oxopent-4-enenitriles with Alkynes for the Synthesis of Polysubstituted 2H-Pyrans
    Yan, Kelu
    Liu, Xiao
    Wen, Jiangwei
    Li, Qiuyun
    Wang, Junjie
    Zheng, Yang
    Wang, Xiu
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (17) : 1986 - 1992
  • [30] The first regioselective double electrophilic substitution of the C2-symmetric pseudo-meta-disubstituted [2.2]paracyclophanes
    Vorontsova, NV
    Vorontsov, EV
    Sergeeva, EV
    Rozenberg, VI
    [J]. TETRAHEDRON LETTERS, 2006, 47 (14) : 2357 - 2360