Synthesis of five- and six-membered lactams via solvent-free microwave Ugi reaction

被引:24
作者
Jida, Mouhamad
Malaquin, Sandra
Deprez-Poulain, Rebecca [1 ]
Laconde, Guillaume
Deprez, Benoit
机构
[1] Univ Lille Nord France, Fac Pharm, INSERM U761, F-59006 Lille, France
关键词
4-Center 3-component Ugi; Ketoacids; Microwave; Solvent-free; Lactams; MULTICOMPONENT REACTIONS; AMINO-ACIDS; CONDENSATION; EFFICIENT; PART;
D O I
10.1016/j.tetlet.2010.07.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five- and six-membered lactams were synthesized via a 4-center 3-component Ugi reaction by combining amines, isocyanides, and ketoacids under solvent-free microwave conditions. The reaction was carried out in much shorter times and the yields were improved in comparison to classical conditions. (c) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5109 / 5111
页数:3
相关论文
共 25 条
[1]   Fast, easy, solvent-free, microwave-promoted Michael addition of anilines to α,β-unsaturated alkenes:: synthesis of N-aryl functionalized β-amino esters and acids [J].
Amore, Kristen M. ;
Leadbeater, Nicholas E. ;
Miller, Tyson A. ;
Schmink, Jason R. .
TETRAHEDRON LETTERS, 2006, 47 (48) :8583-8586
[2]   Synthesis of functionalized pyroglutamic acids, part 1:: The synthetic utility of N-acylindole and the Ugi reaction with a chiral levulinic acid [J].
Buller, Matthew J. ;
Gilley, Cynthla B. ;
Nguyen, Brian ;
Olshansky, Lisa ;
Fraga, Breena ;
Kobayashi, Yoshihisa .
SYNLETT, 2008, (15) :2244-2248
[3]   Microwave-assisted N-Boc deprotection under mild basic conditions using K3PO4•H2O in MeOH [J].
Dandepally, Srinivasa Reddy ;
Williams, Alfred L. .
TETRAHEDRON LETTERS, 2009, 50 (09) :1071-1074
[4]   Microwave-induced one-pot synthesis of 4-[3-(aryl)-1,2,4-oxadiazol-5-yl]-butan-2-ones under solvent free conditions [J].
de Freitas, Juclelton Jose R. ;
de Freitas, Juliano Carlo R. ;
da Silva, Ladjane P. ;
de Freitas, Joao R. ;
Kimura, Gisele Y. V. ;
Srivastava, Rajendra M. .
TETRAHEDRON LETTERS, 2007, 48 (35) :6195-6198
[5]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[6]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[7]  
2-U
[8]   An atom efficient and solvent-free synthesis of structurally diverse amides using microwaves [J].
Gelens, E ;
Smeets, L ;
Sliedregt, LAJM ;
van Steen, BJ ;
Kruse, CG ;
Leurs, R ;
Orru, RVA .
TETRAHEDRON LETTERS, 2005, 46 (21) :3751-3754
[9]   ALPHA-AMINO ACIDS AND DERIVATIVES .2. ISONITRILE REACTIONS WITH GLYOXYLIC ACID DERIVATIVES [J].
GROSS, H ;
GLOEDE, J ;
KEITEL, I ;
KUNATH, D .
JOURNAL FUR PRAKTISCHE CHEMIE, 1968, 37 (3-4) :192-&
[10]   Multi-component reactions 13:: Synthesis of γ-lactams as part of a multi-ring system via Ugi-4-centre-3-component reaction [J].
Hanusch-Kompa, C ;
Ugi, I .
TETRAHEDRON LETTERS, 1998, 39 (18) :2725-2728