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Efficient construction of pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines via cascade cycloaddition and annulation reaction

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Abstract

Novel polysubstituted pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines were efficiently synthesized by a one-pot three-component reaction of proline, isatins and chalcones in refluxing methanol and by a sequential domino annulation reaction with methyl propiolate in refluxing acetonitrile. The reaction with isatins without an N-protecting group afforded hexahydropyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines, while the reaction with N-benzylisatins gave octahydropyrrolo[1′,2′:1,2]azocino[4,5-c]quinolones with an additional propiolate unit connecting to a dihydropyridyl ring. The reaction mechanism with domino [3 + 2]cycloaddition, ring-expansion and annulation processes was rationally proposed for the formation of polycyclic products.

Graphical abstract: Efficient construction of pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines via cascade cycloaddition and annulation reaction

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Publication details

The article was received on 14 Jul 2019, accepted on 30 Aug 2019 and first published on 04 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO00891H
Org. Chem. Front., 2019, Advance Article

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    Efficient construction of pyrrolo[1′,2′:1,2]azocino[4,5-c]quinolines via cascade cycloaddition and annulation reaction

    W. Wu, Y. Han, J. Sun and C. Yan, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00891H

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