A facile tandem synthesis of α-benzyl benzimidazole acetonitriles

被引:11
作者
Dubey, P. K. [1 ]
Reddy, P. V. V. Prasada [1 ]
Srinivas, K. [1 ]
机构
[1] Osmania Univ, Coll Engn, Dept Chem, Kukatpally, Hyderabad 500085, Andhra Pradesh, India
关键词
benzimidazoleacetonitriles; aromatic aldehydes; basic alumina; solvent-free; NaBH4;
D O I
10.3998/ark.5550190.0008.f19
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and convenient tandem method for the synthesis of alpha-benzylbenzimi dazoleacetonitriles has been developed. In this method, a benzimidazoleacetonitrile 1 was condensed with an aromatic aldehyde in the presence of basic alumina under solvent-free conditions by simple physical grinding of reactants using a mortar and pestle. Subsequent reduction of the in situ formed acrylonitrile derivative with NaBH4 in 95% ethanol at room temperature gives the corresponding 2-(1H-benzimidazol-2-yl)-3-aryl-propionitrile 3 by regiospecific reduction of the double bond.
引用
收藏
页码:192 / 198
页数:7
相关论文
共 41 条
[1]   NOVEL BORANE SELENIUM COMPLEX - HIGHLY SELECTIVE REDUCTION OF TERTIARY AMIDES AND NITRILES TO THE CORRESPONDING AMINES WITH SODIUM-BOROHYDRIDE DIALKYLSELENIUM DIBROMIDE [J].
AKABORI, S ;
TAKANOHASHI, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :479-482
[2]  
ALEXANDER DT, 2004, SYNTHESIS-STUTTGART, V3, P373
[3]   SYNTHESIS OF POLYAZAHETEROCYCLES BY MICHAEL ADDITION OF CH ACIDS TO ALPHA,BETA-UNSATURATED NITRILES - SYNTHESIS OF PYRIDO[1,2-A]BENZIMIDAZOLE AND PYRIMIDO[5',4'/5,6]PYRIDO[1,2-A]BENZIMIDAZOLE DERIVATIVES [J].
BOGDANOWICZSZWED, K ;
CZARNY, A .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (03) :279-282
[4]  
Buchi J, 1960, ARCH PHARM, V293, P758
[5]   REDUCTION OF ALDEHYDES, KETONES AND ACID CHLORIDES BY SODIUM BOROHYDRIDE [J].
CHAIKIN, SW ;
BROWN, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (01) :122-125
[6]   DNA MINOR GROOVE-BINDING LIGANDS - A DIFFERENT CLASS OF MAMMALIAN DNA TOPOISOMERASE-I INHIBITORS [J].
CHEN, AY ;
YU, C ;
GATTO, B ;
LIU, LF .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (17) :8131-8135
[7]   The preparation and reactions of 2-benzimidazolecarboxylic acid and 2-benzimidazoleacetic acid [J].
Copeland, RAB ;
Day, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1072-1075
[8]   Alternate method for the synthesis of N-alkyl/aralkyl-2-(α-hydroxy alkyl/aralkyl)benzimidazoles via regiospecific acetylation [J].
Dubey, P. K. ;
Prasada Reddy, P. V. V. ;
Srinivas, K. .
SYNTHETIC COMMUNICATIONS, 2007, 37 (10) :1675-1681
[9]   Unexpected regiospecific reduction of the double bond by NaBH4 in 2-(1-methyl/1H-benzimidazole-2-yl)-3-aryl-acrylonitrile [J].
Dubey, P. K. ;
Reddy, P. V. V. Prasada .
SYNTHETIC COMMUNICATIONS, 2007, 37 (13) :2259-2266
[10]  
Dubey PK, 2007, INDIAN J CHEM B, V46, P488