Tetrabutylammonium Fluoride (TBAF) Catalysed Synthesis of 2-Arylbenzimidazole in Water under Ultrasound Irradiation

被引：22

作者：

Joshi, Ratnadeep S. ^{[1
]}

Mandhane, Priyanka G. ^{[1
]}

Dabhade, Sanjay K. ^{[1
]}

Gill, Charansingh H. ^{[1
]}

机构：

[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, MS, India

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2010年 / 57卷 / 6B期

关键词：

Tetrabutylammonium fluoride (TBAF); Water; 2-Benzimidazole; Ultrasonication; Green synthesis; DNA-BINDING; BENZIMIDAZOLES; INHIBITORS; HOECHST-33258; NITROBENZENE; PHARMACOLOGY; SPECIFICITY; OMEPRAZOLE; MICROWAVE; BASE;

D O I：

10.1002/jccs.201000181

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One-pot multistep reactions involving a new environmentally friendly catalytic procedure have been developed for the synthesis of benzimidazole. The reaction of the substituted aldehyde with o-phenylenediamine in water under ultrasonic irradiation at ambient temperature for appropriate time using 5 mol% of TBAF furnish the desired product in good to excellent yield. The process is green, mild, inexpensive, excellent chemo selectivity, and excellent yields are the main advantages of this procedure.

引用

页码：1227 / 1231

页数：5

共 53 条

[1] TBAF-Catalyzed synthesis of 5-substituted IH-tetrazoles under solventless conditions [J].

Amantini, D ;

Beleggia, R ;

Fringuelli, F ;

Pizzo, F ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2896-2898

[2] A short synthesis of the PARP inhibitor 2-(4-trifluoromethylphenyl)benzimidazole-4-carboxamide (NU1077) [J].

Austen, SC ;

Kane, JM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (04) :979-980

[3] The effects of benzimidazole anthelmintics on P4501A in rat hepatocytes and HepG2 cells [J].

Baliharová, V ;

Skálová, L ;

Maas, RFM ;

De Vrieze, G ;

Bull, S ;

Fink-Gremmels, J .

RESEARCH IN VETERINARY SCIENCE, 2003, 75 (01) :61-69

[4] MOLECULAR RECOGNITION BETWEEN LIGANDS AND NUCLEIC-ACIDS - NOVEL PYRIDINE-CONTAINING AND BENZOXAZOLE-CONTAINING AGENTS RELATED TO HOECHST-33258 THAT EXHIBIT ALTERED DNA-SEQUENCE SPECIFICITY DEDUCED FROM FOOTPRINTING ANALYSIS AND SPECTROSCOPIC STUDIES [J].

BATHINI, Y ;

RAO, KE ;

SHEA, RG ;

LOWN, JW .

CHEMICAL RESEARCH IN TOXICOLOGY, 1990, 3 (03) :268-280

[5]

Beaulieu PL, 2003, SYNTHESIS-STUTTGART, P1683

[6] 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

[7] 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-+

[8]

Bourgrin K., 1998, TETRAHEDRON, V54, P8055

[9] INSITU GENERATION AND SYNTHETIC APPLICATION OF 2-PHENYLBENZIMIDAZOLINE TO THE SELECTIVE REDUCTION OF CARBON CARBON DOUBLE-BONDS OF ELECTRON-DEFICIENT OLEFINS [J].

CHIKASHITA, H ;

NISHIDA, S ;

MIYAZAKI, M ;

MORITA, Y ;

ITOH, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (02) :737-746

[10] Synthesis of mono-cationic and dicationic analogs of Hoechst 33258 [J].

Czarny, A ;

Wilson, WD ;

Boykin, DW .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (04) :1393-1397

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