Synthesis of substituted 3-(3-chloro-1H-pyrazol-5-yl)quinoxalin-2(1H)ones

被引：3
|
作者：
Steger, Stefan [1 ]
Matuszczak, Barbara [1 ]
机构：
[1] Univ Innsbruck, CCB, Inst Pharm Pharmaceut Chem, A-6020 Innsbruck, Austria
来源：
TETRAHEDRON | 2014年 / 70卷 / 38期
关键词：
Monomethoxy substituted 3-(3-chloro-1-H-pyrazol-5-yl)quinoxalin-2(1H)ones; 3,6-Dichloropyridazine-4-carboxamides; Pyridazine to pyrazole ring transformation; DERIVATIVES;
D O I：
10.1016/j.tet.2014.07.072
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Synthetic strategies to gain access to all four isomers of 3-(3-chloro-1H-pyrazol-5-yl)quinoxalin-2(1H) ones with monosubstituted benzo core (i.e., compounds 8a-d) are described. Preparation of these heterocyclic compounds succeeded starting from only two different substituted 2-nitroanilines (i.e., 3-methoxy- and 4-methoxy-2-nitroaniline) in three or five steps, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6763 / 6768
页数：6
相关论文
共 50 条
  • [1] "Synthesis of substituted 3-(3-chloro-1H-pyrazol-5-y1) quinoxalin-2(1H)ones" (vol 70 ,pg 6763, 2014)
    Steger, Stefan
    Matuszczak, Barbara
    TETRAHEDRON, 2016, 72 (50) : 8364 - 8364
  • [2] Darzens Reaction in the Synthesis of 3-(α-Chloroalkyl)quinoxalin-2(1H)-ones
    Saifina, D. F.
    Ganieva, V. R.
    Mamedov, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (08) : 1244 - 1247
  • [3] Darzens reaction in the synthesis of 3-(α-chloroalkyl)quinoxalin-2(1H)-ones
    D. F. Saifina
    V. R. Ganieva
    V. A. Mamedov
    Russian Journal of Organic Chemistry, 2009, 45 : 1244 - 1247
  • [4] Concise route to a series of novel 3-(tetrazol-5-yl)quinoxalin-2(1H)-ones
    Gunawan, Steven
    Nichol, Gary
    Hulme, Christopher
    TETRAHEDRON LETTERS, 2012, 53 (13) : 1664 - 1667
  • [5] 3-(α-Chlorobenzyl)quinoxalin-2(1H)-ones as Versatile Reagents for the Synthesis of 3-Benzylquinoxalin-2(1H)-ones and Thiazolo[3,4-a]quinoxalin-4(5H)-ones
    Mamedov, Vakhid A.
    Zhukova, Nataliya A.
    Syakaev, Victor V.
    Beschastnova, Tat'yana N.
    Kadyrova, Milyausha S.
    Isaeva, Anastasiya O.
    Mamedova, Sevil, V
    Gavrilova, Elena L.
    Latypov, Shamil K.
    Sinyashin, Oleg G.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (08) : 2221 - 2234
  • [6] 3-(α-azidoalkyl)quinoxalin-2(1H)-ones and related alkylquinoxalinyl ketones
    Mamedov V.A.
    Saifina D.F.
    Berdnikov E.A.
    Chemistry of Heterocyclic Compounds, 2007, 43 (04) : 470 - 473
  • [7] 3-(1H-1,5-Benzodiazepin-2(3H)-ylidenemethyl)-quinoxalin-2(1H)-ones in reactions with nucleophiles. Synthesis and structure of 3-(hetarylmethyl)quinoxalin-2-ones
    Obydennov, Dmitrii L.
    Sosnovskikh, Vyacheslav Ya.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (06) : 503 - 513
  • [8] 3-(1H-1,5-Benzodiazepin-2(3H)-ylidenemethyl)-quinoxalin-2(1H)-ones in reactions with nucleophiles. Synthesis and structure of 3-(hetarylmethyl)quinoxalin-2-ones
    Dmitrii L. Obydennov
    Vyacheslav Ya. Sosnovskikh
    Chemistry of Heterocyclic Compounds, 2015, 51 : 503 - 513
  • [9] Metal-free oxidative coupling of quinoxalin-2(1H)-ones with arylaldehydes leading to 3-acylated quinoxalin-2(1H)-ones
    Yuan, Jin-Wei
    Fu, Jun-Hao
    Liu, Shuai-Nan
    Xiao, Yong-Mei
    Mao, Pu
    Qu, Ling-Bo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3203 - 3212
  • [10] Photocatalytic C3-H acylmethylation of quinoxalinone with sulfoxonium ylides for the synthesis of 3-(γ-dicarbonyl)-quinoxalin-2(1H)-ones
    Li, Wenli
    Zhang, Dongliang
    Wang, Yihong
    Zhu, Haibo
    Le, Zhanggao
    Xie, Zongbo
    MOLECULAR CATALYSIS, 2024, 563
12345