One-pot synthesis of 2-trifiuoromethyl and 2-difiuoromethyl substituted benzo-1,3-diazoles

被引：59

作者：

Ge, Fenglian

Wang, Zengxue

Wan, Wen

Lu, Wencong

Hao, Jian

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 18期

基金：

中国国家自然科学基金;

关键词：

fluorinated benzo-1,3-diazoles; fluorinated carboxylic acids; fluorinated heterocycles; bromination; synthesis;

D O I：

10.1016/j.tetlet.2007.03.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Trifluoromethyl and 2-difluoromethyl substituted benzimidazole, benzoxazole and benzothiazole derivatives were efficiently prepared through a one-pot reaction of trifluoroacetic acid and difluoroacetic acid, respectively, with commercially available o-phenylenediamines, 2-aminophenols, and 2-aminobenzenethiols in good to excellent yields. Subsequential bromination of 2-difluoromethyl groups by photolysis with NBS led to the formation of bromodifluoromethyl benzo-1,3-diazoles which may be utilized to prepare the new generation of gem-difluoromethylene linked identical or non-identical twin molecules for drug synthesis. (c) 2007 Elsevier Ltd. All rights reserved.

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页码：3251 / 3254

页数：4

相关论文

共 19 条

[1]

[Anonymous], 2003, PRACTICE MED CHEM

[2] Tetrakis(dimethylamino)ethylene (TDAE) mediated addition of difluoromethyl anions to heteroaryl thiocyanates.: A new simple access to heteroaryl-SCF2R derivatives [J].

Billard, T ;

Langlois, BR ;

Médebielle, M .

TETRAHEDRON LETTERS, 2001, 42 (20) :3463-3465

[3] Novel synthesis of 2-trifluoromethylarylimidazoles on montmorillonite K10 in a 'dry medium' under microwave irradiation [J].

Bougrin, K ;

Loupy, A ;

Petit, A ;

Daou, B ;

Soufiaoui, M .

TETRAHEDRON, 2001, 57 (01) :163-168

[4] Tetrakis(dimethylamino)ethylene as a useful reductant of some bromodifluoromethyl heterocycles.: Application to the synthesis of new gem-difluorinated heteroarylated compounds [J].

Burkholder, C ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5385-5394

[5] Synthesis and reactivity of halogeno-difluoromethyl aromatics and heterocycles -: Application to the synthesis of gem-difluorinated bioactive compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (01) :39-48

[6] The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group -: The SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole with the anions derived from heterocyclic thiols and phenolic compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 102 (1-2) :369-376

[7] A novel method for preparation of trifluoromethyl substituted 2,3-dihydro-1,4-diazepine and benzimidazole [J].

Chu, QL ;

Wang, YL ;

Zhu, SZ .

SYNTHETIC COMMUNICATIONS, 2000, 30 (04) :677-687

[8] Bioactivation of S-(2,2-dihalo-1,1-difluoroethyl)-L-cysteines and S-(trihalovinyl)-L-cysteines by cysteine S-conjugate beta-lyase: Indications for formation of both thionoacylating species and thiiranes as reactive intermediates [J].

Commandeur, JNM ;

King, LJ ;

Koymans, L ;

Vermeulen, NPE .

CHEMICAL RESEARCH IN TOXICOLOGY, 1996, 9 (07) :1092-1102

[9] Syntheses of 2-(bromodifluoromethyl)benzoxazole and 5-(bromodifluoromethyl)-1,2,4-oxadiazoles [J].

Dolbier, WR ;

Burkholder, CR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 1999, 95 (1-2) :127-130

[10] A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid.: Application of the methodology as a convenient route to benzimidazoles [J].

Fonseca, T ;

Gigante, B ;

Gilchrist, TL .

TETRAHEDRON, 2001, 57 (09) :1793-1799