A Facile and Efficient Synthesis of 3-Aryloxazolidin-2-ones from Isocyanates and Epoxides Promoted by MgI2 Etherate

被引:22
作者
Zhang, Xingxian [1 ]
Chen, Wei [1 ]
Zhao, Chengfeng [1 ]
Li, Cheng [1 ]
Wu, Xiang [1 ]
Chen, Wei Z. [1 ]
机构
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310032, Zhejiang, Peoples R China
关键词
Epoxide; isocyanate; MgI2; etherate; oxazolidinone; CATALYZED CYCLOADDITION; OXAZOLIDINONES; 2-OXAZOLIDONES; ALLYLATION; ALDEHYDES; OXIRANES;
D O I
10.1080/00397910903470525
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We described a mild and efficient procedure for the synthesis of 3-aryloxazolidin-2-ones via the cycloaddition of isocyanates with epoxides in the presence of MgI2 etherate (MgI2 center dot(OEt2)n) in good yields.
引用
收藏
页码:3654 / 3659
页数:6
相关论文
共 18 条
[1]   Oxazolidinone structure-activity relationships leading to linezolid [J].
Barbachyn, MR ;
Ford, CW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (18) :2010-2023
[2]   Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections [J].
Brickner, SJ ;
Hutchinson, DK ;
Barbachyn, MR ;
Manninen, PR ;
Ulanowicz, DA ;
Garmon, SA ;
Grega, KC ;
Hendges, SK ;
Toops, DS ;
Ford, CW ;
Zurenko, GE .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :673-679
[3]   Lewis base activation of Lewis acids: Catalytic enantioselective allylation and propargylation of aldehydes [J].
Denmark, SE ;
Wynn, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :6199-6200
[4]   Asymmetric catalysis of aldol reactions with chiral Lewis bases [J].
Denmark, SE ;
Stavenger, RA .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :432-440
[5]   CYCLOADDITION REACTION OF 2,3-DISUBSTITUTED OXIRANES WITH ISOCYANATES BY HIGHLY ACTIVATED CATALYST - PH4SBI-BU3SNI [J].
FUJIWARA, M ;
BABA, A ;
TOMOHISA, Y ;
MATSUDA, H .
CHEMISTRY LETTERS, 1986, (11) :1963-1966
[6]  
Herweh J. E., 1971, TETRAHEDRON LETT, V12, P809
[7]   SYNTHESIS AND NUCLEAR MAGNETIC RESONANCE SPECTRA OF 2-OXAZOLIDONES [J].
HERWEH, JE ;
FOGLIA, TA ;
SWERN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4029-&
[8]  
IDRIS JJ, 1957, J CHEM SOC, P2735
[9]   Chemoselective aldol reaction of silyl enolates catalyzed by MgI2 etherate [J].
Li, WDZ ;
Zhang, XX .
ORGANIC LETTERS, 2002, 4 (20) :3485-3488
[10]   ANTIBACTERIALS - SYNTHESIS AND STRUCTURE ACTIVITY STUDIES OF 3-ARYL-2-OXOOXAZOLIDINES .4. MULTIPLY-SUBSTITUTED ARYL DERIVATIVES [J].
PARK, CH ;
BRITTELLI, DR ;
WANG, CLJ ;
MARSH, FD ;
GREGORY, WA ;
WUONOLA, MA ;
MCRIPLEY, RJ ;
EBERLY, VS ;
SLEE, AM ;
FORBES, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (06) :1156-1165