OXIDATIVE COUPLING OF O-PHENYLENEDIAMINE WITH ARYLMETHYLAMINES TO SYNTHESIZE ARYL-SUBSTITUTED BENZIMIDAZOLES UNDER CATALYST-FREE AND SOLVENT-FREE CONDITIONS

被引：19

作者：

Yu, Jiatao ^{[1
]}

Lu, Ming ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing, Jiangsu, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 17期

关键词：

Benzimidazoles; catalyst-free; oxidation; solvent-free; TBHP; SOLID-PHASE SYNTHESIS; MICROWAVE IRRADIATION; ORGANIC-SYNTHESIS; TOPOISOMERASE-II; EFFICIENT; INHIBITORS; AGENTS; BENZOTHIAZOLES; IMINES; AMINES;

D O I：

10.1080/00397911.2014.908310

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solvent-free oxidative synthesis of benzimidazoles from arylmethylamines and o-phenylenediamine has been achieved under catalyst-free conditions. This reaction can use tert-butyl hydroperoxide (TBHP) as the oxidant, and a wide variety of derivatives were obtained in good yields. The reaction mechanism was proposed and this method provides a direct and practical approach for the preparation of substituted benzimidazoles.

引用

页码：2520 / 2528

页数：9

共 49 条

[1]

[Anonymous], 1997, ARZNEIM FORSCH

[2] A simple and efficient one-pot synthesis of 2-substituted benzimidazoles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad Mehdi ;

Kavianinia, Iman .

SYNTHESIS-STUTTGART, 2007, (04) :547-550

[3] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad M. ;

Nejati, Akbar .

GREEN CHEMISTRY, 2010, 12 (07) :1237-1241

[4]

Bai YJ, 2001, SYNLETT, P544

[5] Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis [J].

Baig, R. B. Nasir ;

Varma, Rajender S. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1559-1584

[6] QUATERNARY-SALTS FROM 2-(METHYLPYRIDYL OR QUINOLYL)BENZIMIDAZOLES AND RELATED POLYMETHINE DYES [J].

BARNI, E ;

SAVARINO, P .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (08) :1583-1587

[7]

Beaulieu PL, 2003, SYNTHESIS-STUTTGART, P1683

[8] Benzimidazoles: Oxidative heterocyclization via nitrobenzene and dimethylsufloxide on silica submitted to microwave or ultraviolet irradiation [J].

Ben-Alloum, A ;

Bakkas, S ;

Soufiaoui, M .

TETRAHEDRON LETTERS, 1998, 39 (25) :4481-4484

[9] OXIDATION WITH METAL OXIDES .2. OXIDATION OF CHALCONE PHENYLHYDRAZONES PYRAZOLINES OMICRON-AMINOBENZYLIDINE ANILS AND OMICRON-HYDROXY BENZYLIDINE ANILS WITH MANGANESE DIOXIDE [J].

BHATNAGAR, I ;

GEORGE, MV .

TETRAHEDRON, 1968, 24 (03) :1293-+

[10] Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase [J].

Biasotti, B ;

Dallavalle, S ;

Merlini, L ;

Farina, C ;

Gagliardi, S ;

Parini, C ;

Belfiore, P .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (10) :2247-2254

← 1 2 3 4 5 →