Borax: An Ecofriendly and Efficient Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones under Solvent-Free Conditions

被引：10

作者：

Nath, Jayashree ^{[2
]}

Chaudhuri, Mihir K. ^{[1
,3
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

[2] Indian Inst Technol Guwahati, Ctr Environm, Gauhati 781039, India

[3] Tezpur Univ, Tezpur, India

来源：

SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 20期

关键词：

Biginelli reaction; borax; 3,4-dihydropyrimidin-2(1H)-ones; solvent free; BIGINELLI REACTION; REUSABLE CATALYST; PARALLEL SYNTHESIS; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; DIHYDROPYRIMIDINONES; CHLORIDE;

D O I：

10.1080/00397910903341163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Borax in the presence of a very small amount of 5M sulfuric acid efficiently catalyses the three-component condensation of an aldehyde, beta-ketoester, and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones or 3,4-dihydropyrimidin-2(1H)-thiones in good to excellent yields under solvent-free conditions at 80 degrees C. Compared with the classical Biginelli reaction conditions, this new method has the advantage of excellent yield, short reaction time (1-2h), easy workup, and no use of volatile organic solvent.

引用

页码：2976 / 2982

页数：7

共 30 条

[21] Ionic liquids catalyzed Biginelli reaction under solvent-free conditions [J].

Peng, JJ ;

Deng, YQ .

TETRAHEDRON LETTERS, 2001, 42 (34) :5917-5919

[22] Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].

Reddy, CV ;

Mahesh, M ;

Raju, PVK ;

Babu, TR ;

Reddy, VVN .

TETRAHEDRON LETTERS, 2002, 43 (14) :2657-2659

[23] Silica sulfuric acid:: an efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].

Salehi, P ;

Dabiri, M ;

Zolfigol, MA ;

Fard, MAB .

TETRAHEDRON LETTERS, 2003, 44 (14) :2889-2891

[24] One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions [J].

Su, W ;

Li, JJ ;

Zheng, ZG ;

Shen, YC .

TETRAHEDRON LETTERS, 2005, 46 (36) :6037-6040

[25] A highly efficient solvent-free synthesis of dihydropyrimidinones catalyzed by zinc chloride [J].

Sun, Q ;

Wang, YQ ;

Ge, ZM ;

Cheng, TM ;

Li, RT .

SYNTHESIS-STUTTGART, 2004, (07) :1047-1051

[26] Natural HEU type zeolite catalyzed Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H) one derivatives [J].

Tajbakhsh, M ;

Mohajerani, B ;

Heravi, MM ;

Ahmadi, AN .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 236 (1-2) :216-219

[27] One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones using boric acid as catalyst [J].

Tu, S ;

Fang, F ;

Miao, CB ;

Jiang, H ;

Feng, YJ ;

Shi, DQ ;

Wang, XS .

TETRAHEDRON LETTERS, 2003, 44 (32) :6153-6155

[28] A SOLID-PHASE PROTOCOL OF THE BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS SUITABLE FOR COMBINATORIAL CHEMISTRY [J].

WIPF, P ;

CUNNINGHAM, A .

TETRAHEDRON LETTERS, 1995, 36 (43) :7819-7822

[29] Ultrasound-accelerated synthesis of 3,4-dihydropyrimidin-2(1H)-ones with ceric ammonium nitrate [J].

Yadav, JS ;

Reddy, BVS ;

Reddy, KB ;

Raj, KS ;

Prasad, AR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (16) :1939-1941

[30] An efficient synthesis of 4-substituted pyrazolyl-3,4-dihydropyrimidin-2(1H)-(thio)ones catalyzed by Mg(ClO4)2 under ultrasound irradiation [J].

Zhang, Xinli ;

Li, Yanping ;

Liu, Chenjiang ;

Wang, Jide .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :207-211

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