Pyridinium N-2′-pyridylaminide:: synthesis of 3-aryl-2-aminopyridines through an intramolecular radical process

被引:19
|
作者
Sánchez, A [1 ]
Nuñez, A [1 ]
Alvarez-Builla, J [1 ]
Burgos, C [1 ]
机构
[1] Univ Alcala De Henares, Dept Quim Organ, Madrid 28871, Spain
关键词
arylation; biaryls; ipso-substitution mechanism; radicals and radical reaction; Tris(trimethylsilyl)silane;
D O I
10.1016/j.tet.2004.09.099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tris(trimethylsilyl)silane (TTMSS) and azobisisobutironitrile (AIBN) promote the intramolecular heteroarylation of arenesulfonamides with pyridyl radicals under thermal conditions. The arenesulfonamides are easily prepared from pyridinium N-2'pyridylaminide. The heteroarylation process involves pyridyl radical cyclization and ipso substitution. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11843 / 11850
页数:8
相关论文
共 36 条
  • [11] Self-[3+2] annulation reaction of pyridinium salts: synthesis of N-indolizine-substituted pyridine-2(1H)-ones
    Cao, Yu
    Shi, Qiyuan
    Gao, Kai
    Shao, Jiaan
    Zhu, Huajian
    Zeng, Linghui
    Zhang, Chong
    Xi, Jianjun
    Zhuang, Rangxiao
    Zhang, Jiankang
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (35) : 16651 - 16655
  • [12] SYNTHESIS OF HETEROCYCLES ON THE BASIS OF PRODUCTS OF ARYLATION OF UNSATURATED COMPOUNDS 22. 3-ARYL-2-CHLOROPROPANAL IN THE SYNTHESIS OF N-ARYL-5-(R-BENZYL)-1,3-THIAZOLE-2-AMINES
    Matiychuk, V. S.
    Obushak, N. D.
    Pidlypnyi, N. I.
    Ostapiuk, Yu. V.
    Voloshchuk, R. M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (04) : 495 - 499
  • [13] Synthesis of N-Arylindoles from 2-Alkenylanilines and Diazonaphthalen-2(1H)-ones through Simultaneous Indole Construction and Aryl Introduction
    Yu, Caiyun
    Xu, Yuanshuang
    Zhang, Xinying
    Fan, Xuesen
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (11) : 7392 - 7404
  • [14] Synthesis of heterocycles on the basis of products of arylation of unsaturated compounds 22.* 3-Aryl-2-chloropropanal in the synthesis of N-Aryl-5-(R-benzyl)-1,3-thiazole-2-amines
    V. S. Matiychuk
    N. D.Obushak
    N. I. Pidlypnyi
    Yu. V. Ostapiuk
    R. M. Voloshchuk
    Chemistry of Heterocyclic Compounds, 2010, 46 : 495 - 499
  • [15] Facile synthesis of trifluoroethyl aryl ethers through copper-catalyzed coupling of CF3CH2OH with aryl- and heteroaryl boronic acids
    Wang, Ruixin
    Wang, Liang
    Zhang, Kena
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    TETRAHEDRON LETTERS, 2015, 56 (33) : 4815 - 4818
  • [16] Synthesis of 2-Aryl-2H-benzotrizoles from Azobenzenes and N-Sulfonyl Azides through Sequential Rhodium-Catalyzed Amidation and Oxidation in One Pot
    Ryu, Taekyu
    Min, Jiae
    Choi, Wonseok
    Jeon, Woo Hyung
    Lee, Phil Ho
    ORGANIC LETTERS, 2014, 16 (11) : 2810 - 2813
  • [17] Efficient, One-Pot, BF3•OEt2-Mediated Synthesis of Substituted N-Aryl Lactams
    Chaturvedi, Devdutt
    Chaturvedi, Amit K.
    Mishra, Nisha
    Mishra, Virendra
    SYNLETT, 2012, (18) : 2627 - 2630
  • [18] A concise synthesis of indolin-2-ones via direct acid-catalyzed intramolecular Friedel-Crafts alkylation of 3-chloro-N-(substituted)-2-oxo-N,3-diarylpropanamides
    Mamedov, Vakhid A.
    Galimullina, Venera R.
    Kadyrova, Saniya F.
    Rizvanov, Il'dar Kh.
    Latypov, Shamil K.
    TETRAHEDRON LETTERS, 2022, 99
  • [19] N-Oxide as an Intramolecular Oxidant in the Baeyer-Villiger Oxidation: Synthesis of 2-Alkyl-2H-indazol-3-yl Benzoates and 2-Alkyl-1,2-dihydro-3H-indazol-3-ones
    Schutznerova, Eva
    Krchnak, Viktor
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09) : 3585 - 3596
  • [20] Modular Catalytic Synthesis of 3-Amino-3-aryl-2-oxindoles: Rh Catalysis with Isatin-Derived N-Boc-Protected Ketimines
    Marques, Carolina S.
    Burke, Anthony J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (04) : 806 - 812