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Benzo[7,8]indolizinoquinoline scaffolds based on Mg(ClO 4 ) 2 -promoted regiospecific imide reduction and π-cyclisation of N -acyliminium species. Analogues of the topo-1 poison rosettacin and 22-hydroxyacuminatine alkaloids
Arabian Journal of Chemistry ( IF 6 ) Pub Date : 2019-07-01 , DOI: 10.1016/j.arabjc.2018.03.009
Abdulkareem Hamid , Abdelaziz Souizi , Ata Martin Lawson , Mohamed Othman , Alina Ghinet , Benoît Rigo , Adam Daïch

Abstract A general five-step synthesis of a short library of benzo[7,8]indolizinoquinolinine analogues of the topoisomerase-1 (topo-1) poison rosettacin and 22-hydroxyacuminatine alkaloids from DMAD and ortho -ketoanilines is reported. This consists on successively, the tandem aza-Michael addition/cyclodehydration, the hydrolysis of the resulting diesters into corresponding o -dicarboxylic acids, and the tandem intermolecular amidation/cyclodehydration into N -substituted imides. The regioselective reduction of one imide carbonyl into corresponding α-hydroxy lactams promoted by a Lewis acid Mg(ClO 4 ) 2 was followed ultimately with TFA-promoted π-cationic cyclization via stable N -acyliminiums species as an important key step.

中文翻译:

基于 Mg(ClO 4 ) 2 的苯并 [7,8] 吲哚并喹啉支架促进了 N-acyliminium 物种的区域特异性酰亚胺还原和 π 环化。topo-1 毒物 rosettacin 和 22-hydroxyacuminatine 生物碱的类似物

摘要报道了拓扑异构酶-1 (topo-1) 毒物罗塞塔星和 22-羟基枯草碱生物碱的苯并 [7,8] 吲哚并喹啉类似物的短文库的一般五步合成和来自 DMAD 和邻-酮苯胺。这依次包括串联氮杂-迈克尔加成/环脱水,所得二酯水解成相应的邻二羧酸,以及串联分子间酰胺化/环脱水成N-取代的酰亚胺。在路易斯酸 Mg(ClO 4 ) 2 的促进下,一个酰亚胺羰基的区域选择性还原为相应的 α-羟基内酰胺,最终通过稳定的 N-酰基胺类物质进行 TFA 促进的 π-阳离子环化,这是一个重要的关键步骤。
更新日期:2019-07-01
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