Synthesis of α-substituted N-aryl acrylamide derivatives through Baylis-Hillman reaction

被引:20
作者
Guo, W [1 ]
Wu, WW [1 ]
Fan, NJ [1 ]
Wu, ZG [1 ]
Xia, CZ [1 ]
机构
[1] Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Peoples R China
基金
中国国家自然科学基金;
关键词
aromatic aldehyde; Baylis-Hillman reaction; N-aryl acrylamide;
D O I
10.1081/SCC-200054850
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-aryl acrylamides were found to be the more activated Michael acceptor for Baylis-Hillman reaction than acrylamides and N-alkyl acrylamides. Treatment of N-aryl acrylamides with aromatic aldehydes in the presence of DABCO (1,4-diazabicyclo[2-2.2]octane) afforded the desired Baylis-Hillman products, alpha-substituted acrylamide derivatives, which have important applications as novel radical polymerization monomers and biologically important reagents.
引用
收藏
页码:1239 / 1251
页数:13
相关论文
共 23 条
[1]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[2]  
Ciganek E., 1997, ORG REACTIONS, V51, P201
[3]   2-aminopyridines as highly selective inducible nitric oxide synthase inhibitors. Differential binding modes dependent on nitrogen substitution [J].
Connolly, S ;
Aberg, A ;
Arvai, A ;
Beaton, HG ;
Cheshire, DR ;
Cook, AR ;
Cooper, S ;
Cox, D ;
Hamley, P ;
Mallinder, P ;
Millichip, I ;
Nicholls, DJ ;
Rosenfeld, RJ ;
St-Gallay, SA ;
Tainer, J ;
Tinker, AC ;
Wallace, AV .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3320-3323
[4]   The formyl C-H•••O hydrogen bond as a critical factor in enantioselective Lewis-acid catalyzed reactions of aldehydes [J].
Corey, EJ ;
Lee, TW .
CHEMICAL COMMUNICATIONS, 2001, (15) :1321-1329
[5]   Hydrogen bonding and the conformations of poly(alkyl acrylamides) [J].
Duffy, DM ;
Rodger, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5206-5212
[6]   Acrylamide in the Baylis-Hillman reaction: Expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts [J].
Faltin, C ;
Fleming, EM ;
Connon, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) :6496-6499
[7]   5-substituted 2-aminopyridine C-nucleosides as protonated cytidine equivalents: Increasing efficiency and selectivity in DNA triple-helix formation [J].
Hildbrand, S ;
Blaser, A ;
Parel, SP ;
Leumann, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (24) :5499-5511
[8]   FUNCTIONALIZATION OF THE ALPHA-POSITION OF ACRYLATE SYSTEMS BY THE ADDITION OF CARBONYL-COMPOUNDS - HIGHLY PRESSURE-DEPENDENT REACTIONS [J].
HILL, JS ;
ISAACS, NS .
TETRAHEDRON LETTERS, 1986, 27 (41) :5007-5010
[9]   N-(4-chlorophenyl)acrylamide [J].
Huo, FJ ;
Wu, WW ;
Yin, CX ;
Guo, W ;
Xia, CZ ;
Yang, P .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 :O629-O630
[10]   Efficient Lewis acid-catalyzed stereocontrolled radical polymerization of acrylamides [J].
Isobe, Y ;
Fujioka, D ;
Habaue, S ;
Okamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (29) :7180-7181