Synthesis of 2-Alkylidene-3-acylquinoxalines from N-Aryl-2-nitrosoanilines and 1,3-Diketones

被引：4
|
作者：
Trawczynski, Adam [1 ]
Wrobel, Zbigniew [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
SYNLETT | 2014年 / 25卷 / 19期
关键词：
cyclization; condensation; heterocycles; annulation; ring closure; DERIVATIVES; NITROARENES; ANTAGONISTS; INHIBITORS; ESTERS; POTENT; ACID;
D O I：
10.1055/s-0034-1379238
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the reaction of N-aryl-2-nitrosoanilines with -diketones, a condensation of the nitroso group with diketone carbanion followed by condensation of the amino function with the less crowded carbonyl group leads to 2-alkylidene-3-acyl-1,2-dihydroquinoxalines under mild basic conditions.
引用
收藏
页码：2773 / 2776
页数：4
相关论文
共 50 条
  • [1] N-Aryl-2-nitrosoanilines as intermediates in the synthesis of substituted phenazines from nitroarenes
    Kwast, Andrzej
    Stachowska, Karolina
    Trawczynski, Adam
    Wrobel, Zbigniew
    TETRAHEDRON LETTERS, 2011, 52 (48) : 6484 - 6488
  • [2] Simple Synthesis of 2-Aminoaryliminophosphoranes from N-Aryl-2-nitrosoanilines and Their Application in 2-Aminobenzimidazole Synthesis
    Lukasik, Emilia
    Wrobel, Zbigniew
    SYNLETT, 2014, 25 (02) : 217 - 220
  • [3] Simple Synthesis of N-Aryl-2-nitrosoanilines in the Reaction of Nitroarenes with Aniline Anion Derivatives
    Wrobel, Zbigniew
    Kwast, Andrzej
    SYNTHESIS-STUTTGART, 2010, (22): : 3865 - 3872
  • [4] Reactivity and substituent effects in the cyclization of N-aryl-2-nitrosoanilines to phenazines
    Wrobel, Zbigniew
    Plichta, Karolina
    Kwast, Andrzej
    TETRAHEDRON, 2017, 73 (22) : 3147 - 3152
  • [5] A Two-Step Synthesis of Selected 1,2,3,4-Tetrahydroquinoxaline Derivatives from N-Aryl-2-nitrosoanilines and Arylidenecyanoacetic Esters
    Krolikiewicz, Magdalena
    Blaziak, Kacper
    Danikiewicz, Witold
    Wrobel, Zbigniew
    SYNLETT, 2013, 24 (15) : 1945 - 1948
  • [6] N-Aryl-2-nitrosoanilines as Intermediates in the Two-Step Synthesis of Substituted 1,2-Diarylbenzimidazoles from Simple Nitroarenes
    Wrobel, Zbigniew
    Stachowska, Karolina
    Grudzien, Krzysztof
    Kwast, Andrzej
    SYNLETT, 2011, (10) : 1439 - 1443
  • [7] Simple Synthesis of Quinoxalin-2(1H)-one N-Oxides from N-Aryl-2-nitrosoanilines and Alkylated Cyanoacetic Esters
    Krolikiewicz, Magdalena
    Wrobel, Zbigniew
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (01) : 123 - 126
  • [8] Regioselective Aromatic Nucleophilic Substitution in N-Aryl-2-nitrosoanilines with Oxygen and Nitrogen Nucleophiles
    Wrobel, Zbigniew
    Stachowka, Karolina
    Kwast, Andrzej
    SYNTHESIS-STUTTGART, 2013, 45 (01): : 127 - 133
  • [9] Tandem Synthesis of α-Diazoketones from 1,3-Diketones
    Zhang, Jianlan
    Chen, Wenwen
    Huang, Dayun
    Zeng, Xiaobao
    Wang, Xinyan
    Hu, Yuefei
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17): : 9171 - 9174
  • [10] SYNTHESIS OF OXYGEN HETEROCYCLES FROM 2-ARYLIDENE-1,3-DIKETONES
    CILLER, JA
    MARTIN, N
    QUINTEIRO, M
    SEOANE, C
    SOTO, JL
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1986, 18 (04) : 227 - 236
12345