Solvent-Free Tandem Synthesis of 2-Thiazolines and 2-Oxazolines Catalyzed by a Copper Catalyst

被引:41
作者
Li, Xiangnan [1 ,2 ]
Zhou, Baoyue [1 ,2 ]
Zhang, Jin [1 ,2 ]
She, Mengyao [1 ,2 ]
An, Shujuan [1 ,2 ]
Ge, Haixia [1 ,2 ]
Li, Cong [1 ,2 ]
Yin, Bing [1 ,2 ]
Li, Jianli [1 ,2 ]
Shi, Zhen [1 ,2 ]
机构
[1] NW Univ Xian, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Xian 710069, Shaanxi, Peoples R China
[2] NW Univ Xian, Coll Chem & Mat Sci, Xian 710069, Shaanxi, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
Heterocycles; Copper; Nitriles; Tandem reactions; OXAZOLINES; THIAZOLINES; CYCLODEHYDRATION; LIGANDS; CYCLOADDITION; INHIBITORS; ALCOHOLS; DESIGN; POTENT; ACIDS;
D O I
10.1002/ejoc.201101786
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tandem reactions of nitriles with 2-aminoethanethiol hydrochloride or amino alcohols in the presence of a catalytic amount of cupric methacrylate ((Cu2L4)-L-II, L = methacrylate) were employed to prepare 2-thiazolines and 2-oxazolines under mild reaction conditions. The synthetic procedure showed high selectivity for the synthesis of mono- and bis-thiazolines and oxazolines, and a variety of 2-thiazolines and 2-oxazolines was obtained in good to excellent yields.
引用
收藏
页码:1626 / 1632
页数:7
相关论文
共 41 条
[1]   Versatile solid-phase synthesis of peptide-derived 2-oxazolines. Application in the synthesis of ligands for asymmetric catalysis [J].
Benito, JM ;
Christensen, CA ;
Meldal, M .
ORGANIC LETTERS, 2005, 7 (04) :581-584
[2]   A Selective and Convenient Method for the Synthesis of 2-Phenylaminothiazolines [J].
Bernacki, April L. ;
Zhu, Lingyang ;
Hennings, D. David .
ORGANIC LETTERS, 2010, 12 (23) :5526-5529
[3]   TOTAL SYNTHESIS OF THIANGAZOLE, A NOVEL NATURALLY-OCCURRING HIV-1 INHIBITOR FROM POLYANGIUM SP [J].
BOYCE, RJ ;
MULQUEEN, GC ;
PATTENDEN, G .
TETRAHEDRON, 1995, 51 (26) :7321-7330
[4]   A one step synthesis of thiazolines from esters [J].
Busacca, CA ;
Dong, Y ;
Spinelli, EM .
TETRAHEDRON LETTERS, 1996, 37 (17) :2935-2938
[5]   A rational approach to the design of selective substrates and potent nontransportable inhibitors of the excitatory amino acid transporter EAAC1 (EAAT3). New glutamate and aspartate analogues as potential neuroprotective agents [J].
Campiani, G ;
De Angelis, M ;
Armaroli, S ;
Fattorusso, C ;
Catalanotti, B ;
Ramunno, A ;
Nacci, V ;
Novellino, E ;
Grewer, C ;
Ionescu, D ;
Rauen, T ;
Griffiths, R ;
Sinclair, C ;
Fumagalli, E ;
Mennini, T .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (16) :2507-2510
[6]   The Hoiamides, Structurally Intriguing Neurotoxic Lipopeptides from Papua New Guinea Marine Cyanobacteria [J].
Choi, Hyukjae ;
Pereira, Alban R. ;
Cao, Zhengyu ;
Shuman, Cynthia F. ;
Engene, Niclas ;
Byrum, Tara ;
Matainaho, Teatulohi ;
Murray, Thomas F. ;
Mangoni, Alfonso ;
Gerwick, William H. .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (08) :1411-1421
[7]   Privileged structures: Applications in drug discovery [J].
DeSimone, RW ;
Currie, KS ;
Mitchell, SA ;
Darrow, JW ;
Pippin, DA .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2004, 7 (05) :473-493
[8]   Pyridine-2,6-bis(oxazolines), helpful ligands for asymmetric catalysts [J].
Desimoni, G ;
Faita, G ;
Quadrelli, P .
CHEMICAL REVIEWS, 2003, 103 (08) :3119-3154
[9]   Novel synthesis of 2-thiazolines [J].
Fernandez, X ;
Fellous, R ;
Duñach, E .
TETRAHEDRON LETTERS, 2000, 41 (18) :3381-3384
[10]   OXAZOLINES - THEIR PREPARATION, REACTIONS, AND APPLICATIONS [J].
FRUMP, JA .
CHEMICAL REVIEWS, 1971, 71 (05) :483-&