A remarkable rate acceleration of the one-pot three-component cyclo-condensation reaction at room temperature: An expedient synthesis of mitotic Kinesin Eg5 inhibitor monastrol

被引：48

作者：

Bose, DS ^{[1
]}

Kumar, RK ^{[1
]}

Fatima, L ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Fine Chem Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNLETT | 2004年 / 02期

关键词：

mitotic; monastrol; 3,4-dihydropyrimidin-2(1H)-ones; biginelli reaction;

D O I：

10.1055/s-2004-815416

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and practical route for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones by a one-pot condensation of aldehydes, beta-ketoesters, and urea is described using trimethylsilyl-triflate (I mol%)-mediated cyclocondensation reaction at room temperature within IS minutes. Yields are significantly higher than utilizing classical Biginelli reaction conditions. Synthesis of Mitotic Kinesin Eg5 inhibitor monastrol has been achieved in 95% isolated yield.

引用

页码：279 / 282

页数：4

共 30 条

[1] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

KIMBALL, SD ;

FLOYD, DM ;

MORELAND, S ;

SWANSON, BN ;

GOUGOUTAS, JZ ;

SCHWARTZ, J ;

SMILLIE, KM ;

MALLEY, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2629-2635

[2] SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

OREILLY, BC ;

SCHWARTZ, J .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907

[3] 1,4-CYCLOADDITION OF 1,3-DIAZABUTADIENES WITH ENAMINES - AN EFFICIENT ROUTE TO THE PYRIMIDINE RING [J].

BARLUENGA, J ;

TOMAS, M ;

BALLESTEROS, A ;

LOPEZ, LA .

TETRAHEDRON LETTERS, 1989, 30 (34) :4573-4576

[4]

Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO

[5]

2-A

[6] A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].

Bigi, F ;

Carloni, S ;

Frullanti, B ;

Maggi, R ;

Sartori, G .

TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468

[7]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[8] Comprehensive survey of combinatorial library synthesis: 1998 [J].

Dolle, RE ;

Nelson, KH .

JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (04) :235-282

[9]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[10]

2-U

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