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

文献情報

出版日 2020-08-10

DOI 10.1039/D0QO00858C

インパクトファクター 5.281

著者

Yan-Liang Lin, Yun-Ta Lee, Yi-Ting Huang

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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