DBU-Based Ionic-Liquid-Catalyzed Carbonylation of o-Phenylenediamines with CO2 to 2-Benzimidazolones under Solvent-Free Conditions

被引：134

作者：

Yu, Bo ^{[1
]}

Zhang, Hongye ^{[1
]}

Zhao, Yanfei ^{[1
]}

Chen, Sha ^{[1
]}

Xu, Jilei ^{[1
]}

Hao, Leiduan ^{[1
]}

Liu, Zhimin ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Key Lab Colloid Interface & Thermodynam, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

来源：

ACS CATALYSIS | 2013年 / 3卷 / 09期

基金：

中国国家自然科学基金;

关键词：

carbon dioxide; ionic liquid; catalysis; carbonylation; benzimidazolone; HIGHLY EFFICIENT; CARBON-DIOXIDE; BENZIMIDAZOLONES; INHIBITORS; TRANSFORMATION; HYDROGENATION; CONDENSATION; DISCOVERY;

D O I：

10.1021/cs400256j

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Herein, a new route was presented to synthesize 2-benzimidazolones via the carbonylation of o-phenylenediamines with CO2 catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based ionic liquids under solvent-free conditions. DBU acetate ([DBUH][OAc]) displayed high efficiency for catalyzing the reactions of CO2 with o-phenylenediamines, and a series of benzimidazolones were obtained in high yields. It was demonstrated that [DBUH][OAc] could serve as a bifunctional catalyst for these reactions with the cation activating CO2 and the anion activating o-phenylenediamines. This protocol provides an effective and environmentally friendly alternative route for production of benzimidazolones, and extends the chemical utilization of CO2 in organic synthesis as well.

引用

页码：2076 / 2082

页数：7

共 41 条

[1] Solid-phase parallel synthesis of substituted dihydroimidazolyl dihydrobenzimidazol-2-ones [J].

Acharya, AN ;

Ostresh, JM ;

Houghten, RA .

TETRAHEDRON, 2002, 58 (11) :2095-2100

[2] Discovery of novel benzimidazolones as potent non-nucleoside reverse transcriptase inhibitors active against wild-type and mutant HIV-1 strains [J].

Barreca, Maria Letizia ;

Rao, Angela ;

De Luca, Laura ;

Iraci, Nunzio ;

Monforte, Anna-Maria ;

Maga, Giovanni ;

De Clercq, Erik .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (07) :1956-1960

[3] Synthesis of structurally diverse benzimidazolyl benzimidazolones by application of soluble polymer support [J].

Chen, Hsia-Yuan ;

Kulkarni, Manohar V. ;

Chen, Chih-Hau ;

Sun, Chung-Ming .

TETRAHEDRON, 2008, 64 (27) :6387-6394

[4] Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? [J].

Cokoja, Mirza ;

Bruckmeier, Christian ;

Rieger, Bernhard ;

Herrmann, Wolfgang A. ;

Kuehn, Fritz E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8510-8537

[5]

Curis Inc., 2011, Treatment of cancers having k-ras mutations, Patent No. [WO2011130628, 2011130628]

[6] Synthesis of 3-(4-tert-butylphenyl)-2-propen-1-one, a precursor to Lilial®, via an aldol condensation in an ionic liquid [J].

Davey, PN ;

Forsyth, SA ;

Gunaratne, HQN ;

Hardacre, C ;

McKeown, A ;

McMath, SEJ ;

Rooney, DW ;

Seddon, KR .

GREEN CHEMISTRY, 2005, 7 (04) :224-229

[7] Ionic liquid (molten salt) phase organometallic catalysis [J].

Dupont, J ;

de Souza, RF ;

Suarez, PAZ .

CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691

[8] Catalytic enantioselective Diels-Alder reaction in ionic liquid via a recyclable chiral In(III) complex [J].

Fu, Fan ;

Teo, Yong-Chua ;

Loh, Teck-Peng .

ORGANIC LETTERS, 2006, 8 (26) :5999-6001

[9] Carbonylation of o-phenylenediamine and o-aminophenol with dimethyl carbonate using lead compounds as catalysts [J].

Fu, Y ;

Baba, T ;

Ono, Y .

JOURNAL OF CATALYSIS, 2001, 197 (01) :91-97

[10] Discovery and design of benzimidazolone based inhibitors of p38 MAP kinase [J].

Hammach, Abdelhakim ;

Barbosa, Antonio ;

Gaenzler, Faith Corbo ;

Fadra, Tazmeen ;

Goldberg, Daniel ;

Hao, Ming-Hong ;

Kroe, Rachel R. ;

Liu, Pingrong ;

Qian, Kevin C. ;

Ralph, Mark ;

Sarko, Christopher ;

Soleymanzadeh, Fariba ;

Moss, Nell .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (24) :6316-6320

← 1 2 3 4 5 →