Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases

被引：45
作者：
Inamoto, Kiyofumi [1 ]
Araki, Yuta [1 ]
Kikkawa, Shoko [1 ]
Yonemoto, Misato [1 ]
Tanaka, Yoshiyuki [1 ]
Kondo, Yoshinori [1 ]
机构：
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 27期
基金：
日本学术振兴会;
关键词：
DIRECT ARYLATION; DEPROTONATIVE FUNCTIONALIZATION; ELECTROPHILIC REACTION; PYRIDINE; T-BU-P4; QUINOLINE; AZINE; ACTIVATION; REAGENTS; EXCHANGE;
D O I：
10.1039/c3ob40782a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Organocatalytic functionalization of heteroaromatic N-oxides was investigated using in situ generated onium amide bases, and C-nucleophiles were efficiently introduced by the sequential addition-elimination reaction under metal-free conditions, affording 2-substituted nitrogen heteroaromatics generally in good to high yields.
引用
收藏
页码：4438 / 4441
页数：4
相关论文
共 39 条
  • [1] Direct arylations of electron-deficient (hetero)arenes with aryl or alkenyl tosylates and mesylates
    Ackermann, Lutz
    Fenner, Sabine
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 430 - 432
  • [2] ALBINI A, 1993, SYNTHESIS-STUTTGART, P263
  • [3] Albini A., 1991, HETEROCYCLIC N OXIDE
  • [4] Selective synthesis of 2-substituted pyridine N-oxides via directed ortho-metallation using Grignard reagents
    Andersson, Hans
    Gustafsson, Magnus
    Olsson, Roger
    Almqvist, Fredrik
    [J]. TETRAHEDRON LETTERS, 2008, 49 (48) : 6901 - 6903
  • [5] Synthesis of 2-substituted pyridines via a regiospecific alkylation, alkynylation, and arylation of pyridine N-oxides
    Andersson, Hans
    Almqvist, Fredrik
    Olsson, Roger
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1335 - 1337
  • [6] Reactions between Grignard reagents and heterocyclic N-oxides: Stereoselective synthesis of substituted pyridines, piperidines, and piperazines
    Andersson, Hans
    Olsson, Roger
    Almqvist, Fredrik
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (02) : 337 - 346
  • [7] Synthesis of substituted 4-pyridones and 4-aminopyridinium salts via a one-pot pyridine synthesis
    Andersson, Hans
    Das, Sajal
    Gustafsson, Magnus
    Olsson, Roger
    Almqvist, Fredrik
    [J]. TETRAHEDRON LETTERS, 2010, 51 (32) : 4218 - 4220
  • [8] Efficient, mild and completely regioselective synthesis of substituted pyridines
    Andersson, Hans
    Banchelin, Thomas Sainte-Luce
    Das, Sajal
    Olsson, Roger
    Almqvist, Fredrik
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (19) : 3384 - 3386
  • [9] The Regio- and Stereoselective Synthesis of trans-2,3-Dihydropyridine N-oxides and Piperidines
    Andersson, Hans
    Gustafsson, Magnits
    Bostrom, Dan
    Olsson, Roger
    Almqvist, Fredrik
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (18) : 3288 - 3291
  • [10] Functionalisation of heteroaromatic N-oxides using organic superbase catalyst
    Araki, Yuta
    Kobayashi, Koji
    Yonemoto, Misato
    Kondo, Yoshinori
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (01) : 78 - 80
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