Efficient and Expeditious Synthesis of Di- and Trisubstituted Thiazoles in PEG Under Catalyst-Free Conditions

被引:47
作者
Zhu, Dongjian [1 ]
Chen, Jiuxi [1 ]
Xiao, Huilong [1 ]
Liu, Miaochang [1 ]
Ding, Jinchang [1 ]
Wu, Huayue [1 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 335027, Peoples R China
关键词
-Haloketone; PEG-400; thiazoles; thioamides; thioureas; SOLVENT-FREE CONDITIONS; FUNCTIONALIZED THIAZOLES; AMMONIUM THIOCYANATE; ETHYL BROMOPYRUVATE; PROMOTED SYNTHESIS; PHASE SYNTHESIS; ACID-CHLORIDES; IONIC LIQUIDS; 2-AMINOTHIAZOLES; AMINOTHIAZOLES;
D O I
10.1080/00397910802691874
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and expeditious catalyst-free protocol was developed for the construction of di- and trisubstituted thiazoles from -haloketones and thioureas/thioamides in PEG. The reaction was carried out at ambient temperature, and the products were obtained in excellent isolated yields (91-98%). Additionally, PEG could be recovered easily and was reused without evident loss in activity.
引用
收藏
页码:2895 / 2906
页数:12
相关论文
共 38 条
[1]   Synthesis of functionalized thiazoles via attack of heterocyclic nucleophiles on allenyl isothiocyanates [J].
Al-Hourani, Baker Jawabrah ;
Banert, Klaus ;
Gomaa, Nermeen ;
Vrobel, Kai .
TETRAHEDRON, 2008, 64 (23) :5590-5597
[2]   Novel one-pot three-step reaction using supported reagents system: synthesis of 2-aminothiazoles [J].
Aoyama, Tadashi ;
Murata, Sumiko ;
Takido, Toshio ;
Kodomari, Mitsuo .
TETRAHEDRON, 2007, 63 (48) :11933-11937
[3]   Osmium tetroxide in poly(ethylene glycol) (PEG): a recyclable reaction medium for rapid asymmetric dihydroxylation under Sharpless conditions [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Sultana, SS ;
Reddy, NR .
CHEMICAL COMMUNICATIONS, 2003, (14) :1716-1717
[4]   Gallium(III) triflate-catalyzed one-pot selective synthesis of 2 3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones [J].
Chen, Jiuxi ;
Wu, Dengze ;
He, Fei ;
Liu, Miaochang ;
Wu, Huayue ;
Ding, Jinchang ;
Su, Weike .
TETRAHEDRON LETTERS, 2008, 49 (23) :3814-3818
[5]   Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid-water without additional catalyst [J].
Chen, Jiuxi ;
Su, Weike ;
Wu, Huayue ;
Liu, Miaochang ;
Jin, Can .
GREEN CHEMISTRY, 2007, 9 (09) :972-975
[6]   An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions [J].
Chen, Jiuxi ;
Wu, Huayue ;
Zheng, Zhiguo ;
Jin, Can ;
Zhang, Xingxian ;
Su, Weike .
TETRAHEDRON LETTERS, 2006, 47 (30) :5383-5387
[7]   Highly regioselective ring-opening of epoxides with thiophenols in ionic liquids without the use of any catalyst [J].
Chen, JX ;
Wu, HY ;
Jin, C ;
Zhang, XX ;
Xie, YY ;
Su, WK .
GREEN CHEMISTRY, 2006, 8 (04) :330-332
[8]   Solvent-free synthesis of β-hydroxy esters and β-amino esters by indium-mediated reformatsky reaction [J].
Chen, Xi'an ;
Zhang, Changfu ;
Wu, Huayue ;
Yu, Xiaochun ;
Su, Weike ;
Cheng, Jiang .
SYNTHESIS-STUTTGART, 2007, (20) :3233-3239
[9]   A rapid and high-yielding synthesis of thiazoles and aminothiazoles using ammonium-12-molybdophosphate [J].
Das, Biswanath ;
Reddy, V. Saidi ;
Ramu, R. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 252 (1-2) :235-237
[10]   Soluble polymers as scaffolds for recoverable catalysts and reagents [J].
Dickerson, TJ ;
Reed, NN ;
Janda, KD .
CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343