Aza-heterocyclic frameworks through intramolecular pi-system trapping of spiro-N-acyliminiums generated from isoindolinone

Chortani Sarra; Othman Mohamed; Lawson Ata Martin; Romdhane Anis; Ben Jannet Hichem; Knorr Michael; Brieger Lukas; Strohmann Carsten; Daich Adam

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Aza-heterocyclic frameworks through intramolecular pi-system trapping of spiro-N-acyliminiums generated from isoindolinone

机译：通过异吲哚啉酮产生的螺氮酰亚胺的分子内Pi-Systemiums的AZA-杂环骨架

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Spiro-acetoxylactams as key substrates were obtained straightforwardly by the tandem regioselective reduction/O-acylation of spiro-isoindolinone-imides. The latter were produced in large scale in three steps from homophthalic acid. These imides were useful to provide in one step isoindolinones bearing hydroxymethyl-amide functions, tethered at quaternary carbon centre with promising biological issues. Submitted to Bronsted (TFA neat) and Lewis acid (trimethylsilyltrifluoro-methanesulfonic (TMSOTf) 10 mol%), the spiro-acetoxylactams undergo pi-cyclization of spiro-N-acyliminiums to provide diastereoselectively with pi-aromatic original pyrrolopyrido- and pyrroloazepino-isoindoles fused or not to aromatic systems. With pi-olefins, pyrrolopyridines and pyrrolo-azepines fused to isoindoline or containing amino-acids were isolated. A reaction mechanism producing all these systems is also discussed.

机译：通过螺旋-异吲哚啉酮酰亚胺的串联区域选择性还原/O-酰化反应，直接获得了作为关键底物的螺旋-乙酰氧基内酰胺。后者由邻苯二甲酸经三步大规模生产而成。这些酰亚胺有助于一步提供具有羟甲基酰胺功能的异吲哚酮，这些异吲哚酮栓系在四元碳中心，具有很好的生物问题。提交给Bronsted（TFA-neat）和Lewis酸（三甲基硅基三氟甲烷磺酸（TMSOTf）10 mol%），螺环乙酰氧基内酰胺进行螺环-N-酰亚胺的pi环化，以提供非对映选择性的pi芳香族原始吡咯吡啶和吡咯氮杂异吲哚与芳香族体系融合或不融合。利用pi烯烃，分离出与异吲哚啉融合或含有氨基酸的吡咯吡啶和吡咯氮卓类化合物。还讨论了产生所有这些体系的反应机理。

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《New Journal of Chemistry》 |2021年第5期|共11页
作者
Chortani Sarra; Othman Mohamed; Lawson Ata Martin; Romdhane Anis; Ben Jannet Hichem; Knorr Michael; Brieger Lukas; Strohmann Carsten; Daich Adam;
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Normandie Univ URCOM UNILEHAVRE FR CNRS 3038 EA 3221 F-76600 Le Havre France;

Normandie Univ URCOM UNILEHAVRE FR CNRS 3038 EA 3221 F-76600 Le Havre France;

Normandie Univ URCOM UNILEHAVRE FR CNRS 3038 EA 3221 F-76600 Le Havre France;

Univ Monastir Fac Sci Monastir Lab Heterocycl Chem LR11ES39 Ave Environm Monastir 5019 Tunisia;

Univ Monastir Fac Sci Monastir Lab Heterocycl Chem LR11ES39 Ave Environm Monastir 5019 Tunisia;

Univ Bourgogne Franche Comte Inst UTINAM UMR CNRS 6213 16 Route Gray F-25030 Besancon France;

Tech Univ Dortmund Anorgan Chem Otto Hahn Str 6 D-44227 Dortmund Germany;

Tech Univ Dortmund Anorgan Chem Otto Hahn Str 6 D-44227 Dortmund Germany;

Normandie Univ URCOM UNILEHAVRE FR CNRS 3038 EA 3221 F-76600 Le Havre France;

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正文语种 eng
中图分类化学;
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Aza-heterocyclic frameworks through intramolecular pi-system trapping of spiro-N-acyliminiums generated from isoindolinone

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