An efficient, surfactant mediated Biginelli condensation for the one pot synthesis of dihydropyrimidine derivatives

被引：8
作者：
Bhattacharjee, Deboshikha [1 ]
Myrboh, Bekington [1 ]
机构：
[1] North Eastern Hill Univ, Dept Chem, Ctr Adv Studies Chem, Shillong 793022, Meghalaya, India
来源：
TETRAHEDRON LETTERS | 2022年 / 104卷
关键词：
SODIUM DODECYL-SULFATE; CALCIUM-CHANNEL BLOCKERS; HIGH-YIELDING PROTOCOL; SOLVENT-FREE SYNTHESIS; ACIDIC IONIC LIQUID; MULTICOMPONENT SYNTHESIS; 3-COMPONENT SYNTHESIS; REUSABLE CATALYST; HIGHLY EFFICIENT; SULFURIC-ACID;
D O I：
10.1016/j.tetlet.2022.154020
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sodium dodecyl sulfate (SDS) has been demonstrated as an efficient surfactant mediated catalyst for the synthesis of dihydropyrimidinone derivatives by the Biginelli condensation of aldehydes, beta-dicarbonyls, and urea/thiourea. The one-pot three component reaction was accomplished in aqueous micellar media affording excellent yield of the products. The reaction being facile and simple is also supplemented with merits like eco-friendly catalyst, aqueous reaction media and non-chromatographic methods of purification. The versatility of this method was examined with various substituted aldehydes and has proved to be proficient with satisfactory results. (C) 2022 Elsevier Ltd. All rights reserved.
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页数：7
相关论文
共 67 条
[1]   Sulphated silica tungstic acid as a highly efficient and recyclable solid acid catalyst for the synthesis of tetrahydropyrimidines and dihydropyrimidines [J].
Ahmed, Nayeem ;
Siddiqui, Zeba N. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 387 :45-56
[2]   Conductometric and fluorometric studies of sodium dodecyl sulphate in aqueous solution and in the presence of amino acids [J].
Ali, Anwar ;
Malik, Nisar Ahmad ;
Uzair, Sahar ;
Ali, Maroof .
MOLECULAR PHYSICS, 2014, 112 (20) :2681-2693
[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]   A reusable magnetic nickel nanoparticle based catalyst for the aqueous synthesis of diverse heterocycles and their evaluation as potential anti-bacterial agent [J].
Bhattacharjee, Deboshikha ;
Sheet, Sanjoy Kumar ;
Khatua, Snehadrinarayan ;
Biswas, Koel ;
Joshi, Santaram ;
Myrboh, Bekington .
BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (18) :5018-5028
[6]   L-proline as an efficient asymmetric induction catalyst in the synthesis of chromeno[2,3-d]pyrimidine-triones, xanthenes in water [J].
Bhattacharjee, Deboshikha ;
Sutradhar, Dipankar ;
Chandra, Asit K. ;
Myrboh, Bekington .
TETRAHEDRON, 2017, 73 (25) :3497-3504
[7]   L-Proline as an efficient enantioinduction organo-catalyst in the solvent-free synthesis of pyrazolo [3,4-b]quinoline derivatives via one-pot multi-component reaction [J].
Bhattacharjee, Deboshikha ;
Kshiar, Baskhemlang ;
Myrboh, Bekington .
RSC ADVANCES, 2016, 6 (98) :95944-95950
[8]   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
[9]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[10]   A facile approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones using a microwave promoted Biginelli protocol in ionic liquid [J].
Dadhania, Abhishek N. ;
Patel, Vaibhav K. ;
Raval, Dipak K. .
JOURNAL OF CHEMICAL SCIENCES, 2012, 124 (04) :921-926
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