Benzo[7,8]indolizinoquinoline scaffolds based on Mg(ClO4)2-promoted regiospecific imide reduction and π-cyclization of N-acyliminium species. Analogues of the topo-1 poison rosettacin and 22-hydroxyacuminatine alkaloids

Abdulkareem Hamid; Abdelaziz Souizi; Ata Martin Lawson; Mohamed Othman; Alina Ghinet; Benoît Rigo; Adam Daïch

doi:10.1016/j.arabjc.2018.03.009

Journal articles

Benzo[7,8]indolizinoquinoline scaffolds based on Mg(ClO4)2-promoted regiospecific imide reduction and π-cyclization of N-acyliminium species. Analogues of the topo-1 poison rosettacin and 22-hydroxyacuminatine alkaloids

Abdulkareem Hamid ^{1, 2} Abdelaziz Souizi ³ Ata Martin Lawson ^{1, 2} Mohamed Othman ^{1, 2} Alina Ghinet ^{4, 5, 6} Benoît Rigo ^{4, 6} Adam Daïch ^{1, 2, *}

* Corresponding author

1 URCOM - Unité de Recherche en Chimie Organique et Macromoléculaire

2 INC3M - Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire

3 UIT - Université Ibn Tofaïl

4 LIRIC - Lille Inflammation Research International Center - U 995

5 Alexandru Ioan Cuza University of Iași [Romania]

6 HEI - Hautes Etudes d’Ingénieur [Lille]

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(ClO4)2 was followed ultimately with TFA-promoted π-cationic cyclization via stable N-acyliminiums species as an important key step.

Keywords : Alkaloids analogues Lewis and Brønsted acids catalysis π-Cationic cyclization N-Acyliminium species Regiospecific imide reduction

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Chemical Sciences

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Benzo[7,8]indolizinoquinoline scaffolds based on Mg(ClO4)2-promoted regiospecific imide reduction and π-cyclization of N-acyliminium species. Analogues of the topo-1 poison rosettacin and 22-hydroxyacuminatine alkaloids

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Benzo[7,8]indolizinoquinoline scaffolds based on Mg(ClO4)2-promoted regiospecific imide reduction and π-cyclization of N-acyliminium species. Analogues of the topo-1 poison rosettacin and 22-hydroxyacuminatine alkaloids

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