Green synthesis of 2-pyrazinones in deep eutectic solvents: From α-chloro oximes to peptidomimetic scaffolds

被引:24
作者
Perrone, Serena [1 ]
Capua, Martina [1 ]
Messa, Francesco [1 ,2 ]
Salomone, Antonio [1 ]
Troisi, Luigino [1 ]
机构
[1] Univ Salento, Dipartimento Sci & Tecnol Biol & Ambientali, I-73100 Lecce, Italy
[2] Univ Bari Aldo Moro, Dipartimento Farm Sci Farmaco, Consorzio CINMPIS, Via E Orabona 4, I-70125 Bari, Italy
关键词
alpha-Chloro oxime; 2-Pyrazinone; Deep eutectic solvents; Green chemistry; Peptidomimetics; PALLADIUM-CATALYZED CARBONYLATION; BASE-INDUCED CONDENSATION; FACTOR VIIA COMPLEX; BETA-LACTAMS; PYRAZINONE ANTITHROMBOTICS; STEREOSELECTIVE-SYNTHESIS; SELECTIVE INHIBITORS; THROMBIN INHIBITORS; DERIVATIVES; 2(1H)-PYRAZINONES;
D O I
10.1016/j.tet.2017.09.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and green synthesis of 2-pyrazinones in deep eutectic solvents (DESs) is described. Treatment of aromatic alpha-chloro oximes with aliphatic amines at 110 degrees C in choline chloride based DESs resulted in a straightforward and efficient assembly of 1,3,5-trisubstituted-2(1H)-pyrazinones. The protocol, featuring mild reaction conditions and avoiding common volatile organic solvents, affords a safe and sustainable approach to original peptidomimetic scaffolds. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6193 / 6198
页数:6
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