Synthesis of Oxazolidin-2-ones via a Copper(I)-Catalyzed Tandem Decarboxylative/Carboxylative Cyclization of a Propiolic Acid, a Primary Amine and an Aldehyde

被引:53
作者
Feng, Huangdi [1 ,2 ]
Ermolat'ev, Denis S. [1 ]
Song, Gonghua [2 ]
Van der Eycken, Erik V. [1 ]
机构
[1] Katholieke Univ Leuven, LOMAC, Dept Chem, Celestijnenlaan 200F, B-3001 Louvain, Belgium
[2] E China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China
关键词
carboxylative cyclization; decarboxylative coupling; oxazolidinones; three-component coupling; CARBON-DIOXIDE; OXAZOLIDINONES; ALCOHOLS; CONSTRUCTION; DERIVATIVES; CATALYSIS; FIXATION; RING;
D O I
10.1002/adsc.201100608
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A facile approach to polysubstituted oxazolidin-2-ones is presented via a copper(I)-catalyzed tandem decarboxylative/carboxylative cyclization of a propiolic acid, a primary amine and an aldehyde (PA2-coulpling). This new multicomponent coupling constitutes an efficient methodology to provide the corresponding oxazolidin-2-ones in good yields.
引用
收藏
页码:505 / 509
页数:5
相关论文
共 55 条
[31]   Carboxylative cyclization of propargylamines with supercritical carbon dioxide [J].
Kayaki, Yoshihito ;
Yamamoto, Masafumi ;
Suzuki, Tomoyuki ;
Ikariya, Takao .
GREEN CHEMISTRY, 2006, 8 (12) :1019-1021
[32]   Palladium-Catalyzed Decarboxylative sp-sp2 Cross-Coupling Reactions of Aryl and Vinyl Halides and Triflates with α,β-Ynoic Acids using Silver Oxide [J].
Kim, Hyunseok ;
Lee, Phil Ho .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) :2827-2832
[33]   A practical gold-catalyzed route to 4-substituted oxazolidin-2-ones from N-Boc propargylamines [J].
Lee, Eun-Sun ;
Yeom, Hyun-Suk ;
Hwang, Ji-Hyun ;
Shin, Seunghoon .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3503-3507
[34]   A short synthesis of oxazolidinone derivatives linezolid and eperezolid : A new class of antibacterials [J].
Lohray, BB ;
Baskaran, S ;
Rao, BS ;
Reddy, BY ;
Rao, IN .
TETRAHEDRON LETTERS, 1999, 40 (26) :4855-4856
[35]   Novel anti-infective compounds [J].
Lohray, VB ;
Lohray, BB ;
Srivastava, BK .
PURE AND APPLIED CHEMISTRY, 2005, 77 (01) :195-200
[36]   RUTHENIUM CATALYZED SELECTIVE SYNTHESIS OF ENOL CARBAMATES BY FIXATION OF CARBON-DIOXIDE [J].
MITSUDO, T ;
HORI, Y ;
YAMAKAWA, Y ;
WATANABE, Y .
TETRAHEDRON LETTERS, 1987, 28 (38) :4417-4418
[37]   One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon [J].
Moon, Jeongju ;
Jeong, Miso ;
Nam, Hyungoog ;
Ju, Jinhun ;
Moon, Joong Ho ;
Jung, Hyun Min ;
Lee, Sunwoo .
ORGANIC LETTERS, 2008, 10 (05) :945-948
[38]   Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides [J].
Moon, Jeongju ;
Jang, Mihee ;
Lee, Sunwoo .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1403-1406
[39]  
Nicolaou K.C., 2000, Angew. Chem, V112, P639
[40]  
Nicolaou KC, 2000, ANGEW CHEM INT EDIT, V39, P625, DOI 10.1002/(SICI)1521-3773(20000204)39:3<625::AID-ANIE625>3.0.CO