Studies on pyrrolidinones. Reaction of pyroglutamic acid and vinylogues with aromatics in Eaton's reagent

被引：7

作者：

Ghinet, Alina ^{[1
,2
]}

Van Hijfte, Nathalie ^{[2
,3
]}

Gautret, Philippe ^{[1
,2
]}

Rigo, Benoit ^{[1
,2
]}

Oulyadi, Hassan ^{[4
]}

Rousseau, Jolanta ^{[1
,2
]}

机构：

[1] Univ Lille Nord France, F-59000 Lille, France

[2] UCLille, EA GRIIOT 4481, Lab Pharmacochim, HEI, F-59046 Lille, France

[3] Univ Havre, UFR Sci & Tech, FR CNRS 3038, URCOM,INC3M,EA 3221, F-76058 Le Havre, France

[4] Univ Rouen, IRCOF UMR CNRS 6014, INC3M, FR CNRS 3038, F-76131 Mont St Aignan, France

来源：

TETRAHEDRON | 2012年 / 68卷 / 04期

关键词：

N-ACYLIMINIUM IONS; PENTOXIDE-METHANESULFONIC-ACID; LACTAM-CARBOXYLIC-ACIDS; NUCLEOPHILIC-ADDITION; ELECTROCHEMICAL SYNTHESIS; BIOLOGICAL EVALUATION; POLYPHOSPHORIC ACID; DECARBOXYLATION; DERIVATIVES; OXIDATION;

D O I：

10.1016/j.tet.2011.11.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The optimization of the synthesis of 5-aryl-2-pyrrolidinones through decarbonylation of pyroglutamic acid in Eaton's reagent, in presence of aromatic derivatives, is described. The utilization of these reaction conditions in the arylation of enaminoester vinylogues (17, 24) of pyroglutamic acid was also realized, confirming that these derivatives are subject to decarbonylationi in the same way as the parent acid. Depending on the nature of the aromatic derivative (15, 21, 28, and 32), two different families of compounds were obtained. Many by-products were also formed, suggesting a utilization of this reaction for compounds more stable than the enaminoesters and enaminonitriles used in this study. The possibility of enaminoesters reacting with aromatics in bimolecular reactions to give enaminoketones should also be noted. Five synthesized compounds were evaluated for their antiproliferative activity on the NCI-60 cancer cell lines panel. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1109 / 1116

页数：8

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