New Ugi/Pictet-Spengler multicomponent formation of polycyclic diketopiperazines from isocyanides and α-keto acids

被引：43
作者：
El Kaim, Laurent [1 ]
Gageat, Mathilde [1 ]
Gaultier, Laetitia [1 ]
Grimaud, Laurence [1 ]
机构：
[1] Ecole Natl Super Tecn, Lab Chim & Procedes, F-75739 Paris 15, France
来源：
SYNLETT | 2007年 / 03期
关键词：
diketopiperazine; isocyanide; multicomponent reaction; Ugi; Pictet-Spengler;
D O I：
10.1055/s-2007-968026
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new four-component 1,4-diketopiperazine formation is described via an Ugi/Pictet-Spengler two-step procedure. The use of alpha-ketocarboxylic acids and homoveratryl isocyanide allows the formation of alpha-keto amides along with cyclised 6-hydroxy-piperazines. The mixtures are not separated but directly treated with trifluoroactic acid to afford a tricyclic 2,5-diketopiperazine in a Pictet Spengler-type cyclisation.
引用
收藏
页码：500 / 502
页数：3
相关论文
共 27 条
[1]   STRUCTURE-ACTIVITY STUDIES OF THE NATURAL PRODUCT SUBSTANCE-P ANTAGONIST WIN-64821 [J].
BARROW, CJ ;
MUSZA, LL ;
COOPER, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (04) :377-380
[2]   RAPID AND CONVENIENT SYNTHESES OF POLYOXIN PEPTIDES CONTAINING N-METHYLATED PEPTIDE-BONDS [J].
BOEHM, JC ;
KINGSBURY, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2307-2314
[3]  
Charlton PA, 1996, THROMB HAEMOSTASIS, V75, P808
[4]  
Cho S, 2003, MOL DIVERS, V6, P283
[5]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[6]   Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
TETRAHEDRON, 1996, 52 (39) :12651-12666
[7]   Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .2. Physico-chemical properties and structures [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :534-540
[8]   Recent advances in the synthesis of diketopiperazines [J].
Dinsmore, CJ ;
Beshore, DC .
TETRAHEDRON, 2002, 58 (17) :3297-3312
[9]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[10]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
123