Highly efficient water-mediated approach to access benzazoles: metal catalyst and base-free synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles

被引：34

作者：

Bala, Manju ^{[1
,2
]}

Verma, Praveen Kumar ^{[1
,2
]}

Sharma, Deepika ^{[1
]}

Kumar, Neeraj ^{[1
]}

Singh, Bikram ^{[1
,2
]}

机构：

[1] CSIR Inst Himalayan Bioresource Technol, Nat Prod Chem & Proc Dev Div, Palampur 176061, Himachal Prades, India

[2] CSIR Inst Himalayan Bioresource Technol, Acad Sci & Innovat Res, Palampur 176061, Himachal Prades, India

来源：

MOLECULAR DIVERSITY | 2015年 / 19卷 / 02期

关键词：

Water-mediated; Benzimidazoles; Benzoxazoles; Benzothiazoles; Benzazolones; ONE-POT SYNTHESIS; ANTITUMOR BENZOTHIAZOLES; ORGANIC-SYNTHESIS; AQUEOUS-MEDIA; IN-VITRO; GEM-DIBROMOMETHYLARENES; BIOLOGICAL-PROPERTIES; CONVENIENT SYNTHESIS; PRIVILEGED SCAFFOLD; REDUCTION;

D O I：

10.1007/s11030-015-9572-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An efficient water-catalyzed method has been developed for the synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles in one step. The present method excludes the usage of toxic metal catalysts and bases to produce benzazoles in good to excellent yields. An efficient and versatile water-mediated method has been established for the synthesis of various 2-arylbenzazoles. The present protocol excludes the usage of any catalyst and additive provided excellent selectivities and yields with high functional group tolerance for the synthesis of 2-arylated benzimidazoles, benzoxazoles, and benzothiazoles. Benzazolones were also synthesized using similar reaction protocol. [GRAPHICS] .

引用

页码：263 / 272

页数：10

共 65 条

[1] Rate acceleration of the Baylis-Hillman reaction in polar solvents (water and formamide). Dominant role of hydrogen bonding, not hydrophobic effects, is implicated [J].