N-Aryl-2-nitrosoanilines as Intermediates in the Two-Step Synthesis of Substituted 1,2-Diarylbenzimidazoles from Simple Nitroarenes

被引:29
|
作者
Wrobel, Zbigniew [1 ]
Stachowska, Karolina [1 ]
Grudzien, Krzysztof [2 ]
Kwast, Andrzej [1 ]
机构
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland
[2] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland
关键词
heterocycles; nitroso group; carbanions; condensation; sulfones; cyclization; VICARIOUS NUCLEOPHILIC-SUBSTITUTION; SOLUTION-PHASE SYNTHESIS; ONE-STEP; HIGH-THROUGHPUT; BENZIMIDAZOLES; 1H-BENZIMIDAZOLES; ALDEHYDES;
D O I
10.1055/s-0030-1260764
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Aryl-2-nitrosoanilines, easily available from reaction of nitroarenes with anilide anions, undergo base-promoted condensation reaction with substituted benzyl aryl sulfones, furnishing 1,2-diaryl-1H-benzimidazoles.
引用
收藏
页码:1439 / 1443
页数:5
相关论文
共 25 条
  • [21] InBr3-Mediated One-Pot Synthesis of 2-(Polyhydroxylatedalkyl)-N-aryl-/-alkylpyrroles from 1,2-Cyclopropa-3pyranone and Amines
    Wang, Pingyuan
    Song, Shanshan
    Miao, Zehong
    Yang, Guangfu
    Zhang, Ao
    ORGANIC LETTERS, 2013, 15 (15) : 3852 - 3855
  • [22] Pd-Catalyzed One-Pot Two-Step Synthesis of 2-(1H-indol-3-yl)-2-phenylindolin-3-ones from 2-Alkynyl Arylazides and Indoles
    Yong, Wanxiong
    Li, Ping
    Sheng, Rong
    Rao, Weidong
    Zhang, Xiaoxiang
    CHEMISTRYSELECT, 2018, 3 (41): : 11696 - 11699
  • [23] Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials
    Zhu, Yang
    Deng, Guisheng
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (24) : 18619 - 18630
  • [24] Synthesis and biological activity of some N-aryl-4-(5-methyl-[1,3,4]-oxadiazolin-2-one-3-yl) substituted benzamides from 3-(4-carboxy)phenylsydnone
    Latthe, Prashant R.
    Badami, Bharati V.
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2006, 83 (10) : 1049 - 1051
  • [25] Two-step synthetic approach to 6-substituted pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones from 6-amino-, 6-alkylamino-, and 6-arylamino-1,3-dimethyluracils
    Bischoff, Kerstin
    Girreser, Ulrich
    Heber, Dieter
    Schuett, Martin
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2006, 61 (04): : 486 - 494