Rapid synthesis of hexahydropyrrolo[3,4-b]pyrrole-fused quinolines via a consecutive [3 + 2] cycloaddition and reduction/intramolecular lactamization cascade,Organic Chemistry Frontiers

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Rapid synthesis of hexahydropyrrolo[3,4-b]pyrrole-fused quinolines via a consecutive [3 + 2] cycloaddition and reduction/intramolecular lactamization cascade
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-08-10 , DOI: 10.1039/d0qo00858c
Yan-Liang Lin _{1,

2,

3,

4,

5} , Yun-Ta Lee _{1,

2,

3,

4,

5} , Indrajeet J. Barve _{1,

2,

3,

4,

5} , Yi-Ting Huang _{1,

2,

3,

4,

5} , Chung-Ming Sun _{1,

2,

3,

4,

5}

Affiliation

An unprecedented synthesis of novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines is achieved through the sequential [3 + 2] cycloaddition reaction of azomethine ylides with maleimides followed by intramolecular lactamization. Condensation of the α-amino acid methyl ester with 2-nitrobenzaldehyde leads to an ester stabilized azomethine ylide which further reacts with maleimide to form hexahydropyrrolo[3,4-c]pyrrole. After the reduction of a nitro group, an unusual transamidation reaction is observed, furnishing the novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines. Isolation of the hexahydropyrrolo[3,4-c]pyrrole amide intermediate revealed the pathway of the reaction mechanism.

中文翻译：

通过连续的[3 + 2]环加成反应和还原/分子内酰胺化级联反应快速合成六氢吡咯并[3,4-b]吡咯稠合的喹啉

通过偶氮甲亚胺与马来酰亚胺的依次[3 + 2]环加成反应，然后进行分子内酰胺化，实现了新型六氢吡咯并[3,4- b ]吡咯稠合的喹啉的空前合成。α-氨基酸甲基酯与2-硝基苯甲醛的缩合产生了酯稳定的偶氮甲碱叶立德，其进一步与马来酰亚胺反应形成六氢吡咯并[3，4- c ]吡咯。硝基还原后，观察到不寻常的氨基转移反应，提供了新颖的六氢吡咯并[3,4- b ]吡咯稠合的喹啉。六氢吡咯并[3,4- c ]吡咯酰胺中间体的分离揭示了反应机理的途径。

更新日期：2020-09-30

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