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

来源：

SYNLETT | 2011年 / 10期

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

页码：1439 / 1443

页数：5

共 25 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 N-Aryl-2-nitrosoanilines in the Reaction of Nitroarenes with Aniline Anion Derivatives
Wrobel, Zbigniew
Kwast, Andrzej
SYNTHESIS-STUTTGART, 2010, (22): : 3865 - 3872
[3] 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
[4] 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
[5] Synthesis of 2-Alkylidene-3-acylquinoxalines from N-Aryl-2-nitrosoanilines and 1,3-Diketones
Trawczynski, Adam
Wrobel, Zbigniew
SYNLETT, 2014, 25 (19) : 2773 - 2776
[6] 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
[7] A novel annulation reaction of N-substituted-2-nitrosoanilines with esters of α-isocyano acids. A one-pot, two-step route to 2-benzimidazole-substituted esters of α-amino acids
Bujok, Robert
Cmoch, Piotr
Wrobel, Zbigniew
TETRAHEDRON LETTERS, 2014, 55 (23) : 3410 - 3413
[8] Aryliminophosphoranes as Key Intermediates in the One-Pot Synthesis of 1-Aryl-1,3-dihydro-2H-benzimidazol-2-ones from N-Aryl-2-nitrosoanilines and Carbon Dioxide under Mild Metal-Free Conditions
Lukasik, Emilia
Wrobel, Zbigniew
SYNTHESIS-STUTTGART, 2016, 48 (08): : 1159 - 1166
[9] Use of Formic Acid as a CO Surrogate for the Reduction of Nitroarenes in the Presence of Dienes: A Two-Step Synthesis of N-Arylpyrroles via 1,2-Oxazines
Fouad, Manar Ahmed
Ferretti, Francesco
Galie, Simone
Ragaini, Fabio
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (38)
[10] Efficient Synthesis of 1-Arylquinoxalin-2(1H)-ones via Cyclocondensation of N-Aryl-Substituted 2-Nitrosoanilines with Functionalized Alkyl Acetates
Wrobel, Zbigniew
Stachowska, Karolina
Kwast, Andrzej
Goscik, Agata
Krolikiewicz, Magdalena
Pawlowski, Robert
Turska, Izabela
HELVETICA CHIMICA ACTA, 2013, 96 (05) : 956 - 968

← 1 2 3 →