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

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 alpha-amino acid methyl ester with 2-nitrobenzaldeh...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 19; pp. 2991 - 2996
Main Authors Lin, Yan-Liang, Lee, Yun-Ta, Barve, Indrajeet J., Huang, Yi-Ting, Sun, Chung-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.10.2020
Royal Society of Chemistry
Subjects
Amino acids
Chemistry
Chemistry, Organic
Crystallography
Cycloaddition
Organic chemistry
Organic compounds
Physical Sciences
Quinolines
Reaction mechanisms
Reduction
Science & Technology
Synthesis
DIASTEREOSELECTIVE SYNTHESIS
SMALL MOLECULES
STEREOSELECTIVE-SYNTHESIS
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Summary: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 alpha-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.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d0qo00858c