A Convenient and Efficient Protocol for the One Pot Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones Catalyzed by Ionic Liquids under Ultrasound Irradiation

被引：47

作者：

Dadhania, Abhishek N. ^{[1
]}

Patel, Vaibhav K. ^{[1
]}

Raval, Dipak K. ^{[1
]}

机构：

[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2011年 / 22卷 / 03期

关键词：

one pot synthesis; 3,4-dihydropyrimidin-2-(1H)-ones; ionic liquid; ultrasound; CALCIUM-CHANNEL BLOCKERS; ACID-ESTERS;

D O I：

10.1590/S0103-50532011000300014

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

Derivatives of 3,4-dihydropyrimidin-2-(1H)-ones were synthesized in excellent yields in short reaction time by one pot, three component reaction of aldehydes, ethyl acetoacetate and urea (or thiourea) in room temperature ionic liquids (RTILs) under ultrasound irradiation without any added catalyst. A plausible mechanistic pathway has been postulated based on the catalytic role of the ionic liquid in promoting the reaction. The ionic liquids could be recycled at least six times with retention of their activity.

引用

页码：511 / 516

页数：6

共 30 条

[1]

Atwal K. S., 1987, US Patent, Patent No. 4684656

[2]

ATWAL KS, 1987, HETEROCYCLES, V26, P1189

[3]

DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].

ATWAL, KS ;

SWANSON, BN ;

UNGER, SE ;

FLOYD, DM ;

MORELAND, S ;

HEDBERG, A ;

OREILLY, BC .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811

[4]

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

[5]

ATWAL KS, 1987, Patent No. 4684655

[6]

Baldwin J. J., 1986, US Patent, Patent No. [4609494A, 4609494]

[7]

BALDWIN JJ, 1987, Patent No. 675321

[8]

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

[9]

Bismuth(III) nitrate catalyzed one-pot synthesis of 3,4-dihydro-pyrimidin-2-(1H)-ones:: an improved protocol for the Biginelli reaction [J].

Chari, MA ;

Shobha, D ;

Kumar, TK ;

Dubey, PK .

ARKIVOC, 2005, :74-80

[10]

DIHYDROPYRIMIDINES - NOVEL CALCIUM-ANTAGONISTS WITH POTENT AND LONG-LASTING VASODILATIVE AND ANTIHYPERTENSIVE ACTIVITY [J].

CHO, H ;

UEDA, M ;

SHIMA, K ;

MIZUNO, A ;

HAYASHIMATSU, M ;

OHNAKA, Y ;

TAKEUCHI, Y ;

HAMAGUCHI, M ;

AISAKA, K ;

HIDAKA, T ;

KAWAI, M ;

TAKEDA, M ;

ISHIHARA, T ;

FUNAHASHI, K ;

SATOH, F ;

MORITA, M ;

NOGUCHI, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2399-2406

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