Ultrasound aided solvent-free synergy: an improved synthetic approach to access 3,4-dihydropyrimidin-2(1H)-ones

被引:5
作者
Ramesh, Rathinam [1 ]
Ramesh, Samikannu [1 ]
Malecki, Jan Grzegorz [2 ]
Lalitha, Appaswami [1 ]
机构
[1] Periyar Univ, Dept Chem, Salem 636011, Tamil Nadu, India
[2] Univ Silesia, Dept Crystallog, Szkolna 9, PL-40007 Katowice, Poland
关键词
3,4-Dihydropyrimidin-2(1H)-ones; Solvent-free synthesis; Trichlorotriazine; X-ray analysis; Ultrasound; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYST; EFFICIENT CATALYSTS; BIGINELLI REACTION; SOLID ACID; NANOPARTICLES; DERIVATIVES;
D O I
10.1007/s13738-019-01597-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A remarkably simple synthetic method has been described for the access of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones in excellent yields in the presence of 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient source of hydrochloric acid under ultrasound radiation. In this tandem reaction, a range of aldehydes, -diketo esters and urea were made to condense together via one-pot, solvent-free synthetic strategy. Use of metal-free catalyst, readily accessible substrates, high production rate and ease of work-up are the imperative features of this protocol. [GRAPHICS] .
引用
收藏
页码:1197 / 1205
页数:9
相关论文
共 44 条
[1]   Syntheses of 2,4,6-trisubstituted triazines as antimalarial agents [J].
Agarwal, A ;
Srivastava, K ;
Puri, SK ;
Chauhan, PMS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :531-533
[2]   ZnO nanoparticles embedded in SBA-15 as an efficient heterogeneous catalyst for the synthesis of dihydropyrimidinones via Biginelli condensation reaction [J].
Bhuyan, Diganta ;
Saikia, Mrinal ;
Saikia, Lakshi .
MICROPOROUS AND MESOPOROUS MATERIALS, 2018, 256 :39-48
[3]   Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes [J].
Bigdeli, Mohammad A. ;
Heravi, Majid M. ;
Mahdavinia, Gholam Hossein .
CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1595-1598
[4]   1,4-DIHYDROPYRIDINES - A BASIS FOR DEVELOPING NEW DRUGS [J].
BOSSERT, F ;
VATER, W .
MEDICINAL RESEARCH REVIEWS, 1989, 9 (03) :291-324
[5]   Multicomponent reactions: advanced tools for sustainable organic synthesis [J].
Cioc, Razvan C. ;
Ruijter, Eelco ;
Orru, Romano V. A. .
GREEN CHEMISTRY, 2014, 16 (06) :2958-2975
[6]   Ligand-Enabled Triple C-H Activation Reactions: One-Pot Synthesis of Diverse 4-Aryl-2-quinolinones from Propionamides [J].
Deng, Youqian ;
Gong, Wei ;
He, Jian ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (26) :6692-6695
[7]   OLEX2: a complete structure solution, refinement and analysis program [J].
Dolomanov, Oleg V. ;
Bourhis, Luc J. ;
Gildea, Richard J. ;
Howard, Judith A. K. ;
Puschmann, Horst .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341
[8]   β-Cyclodextrin-propyl sulfonic acid: a new and eco-friendly catalyst for one-pot multi-component synthesis of 3,4-dihydropyrimidones via Biginelli reaction [J].
Gong, Kai ;
Wang, Hualan ;
Wang, Shuxin ;
Ren, Xiaoxue .
TETRAHEDRON, 2015, 71 (29) :4830-4834
[9]   Ultrasound assisted the preparation of 1-butoxy-4-nitrobenzene under a new multi-site phase-transfer catalyst - Kinetic study [J].
Harikumar, Kuppuswamy ;
Rajendran, Venugopal .
ULTRASONICS SONOCHEMISTRY, 2014, 21 (01) :208-215
[10]  
Ho T.-L., 1992, TANDEM ORGANIC REACT