Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO

被引:98
作者
Baars, Hannah [1 ]
Beyer, Astrid [1 ]
Kohlhepp, Stefanie V. [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
C-H ACTIVATION; CATALYZED SYNTHESIS; BUTOXIDE; SUBSTITUTION; CYCLIZATION; HYDROXIDE;
D O I
10.1021/ol403414v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzimidazoles are prepared by intramolecular N-arylations of amidines mediated by potassium hydroxide in DMSO at 120 degrees C. In this manner, diversely substituted products have been obtained in moderate to very good yields.
引用
收藏
页码:536 / 539
页数:4
相关论文
共 46 条
[1]  
Alamgir M, 2007, TOP HETEROCYCL CHEM, V9, P87, DOI 10.1007/7081_2007_088
[2]   H2O2/Fe(NO3)3-Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles [J].
Bahrami, Kiumars ;
Khodaei, Mohammad Mehdi ;
Naali, Fardin .
SYNLETT, 2009, (04) :569-572
[3]   The therapeutic journey of benzimidazoles: A review [J].
Bansal, Yogita ;
Silakari, Om .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (21) :6208-6236
[4]   Transition-Metal-Free Synthesis of Oxindoles by Potassium tert-Butoxide-Promoted intramolecular α-Arylation [J].
Beyer, Astrid ;
Buendia, Julien ;
Bolm, Carsten .
ORGANIC LETTERS, 2012, 14 (15) :3948-3951
[5]   Potassium Hydroxide/Dimethyl Sulfoxide Promoted Intramolecular Cyclization for the Synthesis of Benzimidazol-2-ones [J].
Beyer, Astrid ;
Reucher, Christine M. M. ;
Bolm, Carsten .
ORGANIC LETTERS, 2011, 13 (11) :2876-2879
[6]   An improved procedure for the synthesis of benzimidazoles, using palladium-catalyzed aryl-amination chemistry [J].
Brain, CT ;
Steer, JT .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6814-6816
[7]   An intramolecular palladium-catalysed aryl amination reaction to produce benzimidazoles [J].
Brain, CT ;
Brunton, SA .
TETRAHEDRON LETTERS, 2002, 43 (10) :1893-1895
[8]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[9]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[10]   Room-Temperature Photoinduced Direct C-H-Arylation via Base-Promoted Homolytic Aromatic Substitution [J].
Buden, Maria E. ;
Guastavino, Javier F. ;
Rossi, Roberto A. .
ORGANIC LETTERS, 2013, 15 (06) :1174-1177