Poly(ethylene)glycol/AlCl3 as a new and efficient system for multicomponent Biginelli-type synthesis of pyrimidinone derivatives

被引:16
作者
Amoozadeh, Ali [1 ]
Rahmani, Salman [1 ]
Nemati, Firouzeh [1 ]
机构
[1] Semnan Univ, Dept Organ Chem, Fac Chem, Semnan 35195363, Iran
关键词
aluminum chloride; Biginelli condensation; poly(ethylene)glycol; pyrimidinone; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; IMPROVED PROTOCOL CONDITIONS; CALCIUM-CHANNEL BLOCKERS; CONDENSATION REACTION; ACID-ESTERS; DIHYDROPYRIMIDINONES; GREEN; CATALYST; ALDEHYDES;
D O I
10.1515/hc-2012-0157
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
Biginelli condensation of aldehydes, cyclopentanone and urea or thiourea in poly(ethylene)glycol 400, at 45 degrees C in the presence of aluminum chloride as a highly efficient catalyst has been developed. The reaction is very fast, clean and environmentally benign for the synthesis of a vast variety of pyrimidinone derivatives.
引用
收藏
页码:69 / 73
页数:5
相关论文
共 42 条
[1]
Cyclic ketones and substituted α-keto acids as alternative substrates for novel Biginelli-like scaffold syntheses [J].
Abelman, MM ;
Smith, SC ;
James, DR .
TETRAHEDRON LETTERS, 2003, 44 (24) :4559-4562
[2]
Amoozadeh A, 2010, S AFR J CHEM-S-AFR T, V63, P72
[3]
Poly(Ethylene) Glycol as a Green and Reusable Solvent in the Oxidation of Sulfides to Sulfoxides Using NaClO [J].
Amoozadeh, Ali ;
Nemati, Firouzeh .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (07) :1381-1385
[4]
A Clean, Mild, and Selective Oxidation of Sulfides to Sulfoxides Using NaClO/H2SO4 in Aqueous Media [J].
Amoozadeh, Ali ;
Nemati, Firouzeh .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (10) :2569-2575
[5]
Amoozadeh A, 2009, S AFR J CHEM-S-AFR T, V62, P44
[6]
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
[7]
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
[8]
Banothu J., 2012, HETEROCYCL COMMUN, V18, P93
[9]
A simple and efficient procedure for the synthesis of benzimidazoles using trichloroisocyanuric acid (TCCA) as the oxidant [J].
Bigdeli, Mohammad A. ;
Dostmohammadi, Hamideh ;
Mahdavinia, Gholam Hossein ;
Nemati, Firouzeh .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) :1203-1205
[10]
HClO4-SiO2 catalyzed stereoselective synthesis of β-amino ketones via a direct Mannich-type reaction [J].
Bigdeli, Mohammad A. ;
Nemati, Firouzeh ;
Mahdavinia, Gholam Hossien .
TETRAHEDRON LETTERS, 2007, 48 (38) :6801-6804