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Diastereoselective synthesis of spirocyclic isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinolines via cascade double [3 + 2]cycloadditions

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Abstract

The one-pot base-promoted cascade double [3 + 2] cycloaddition reaction of N-cyanomethylisoquinolinium chloride with (E)-3-arylideneindolin-2-ones and (E)-N-hydroxybenzimidoyl chloride afforded novel polycyclic spiro[indoline-3,8′-isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. When 4-arylidenepyrazol-3-ones, 2-arylidene-1,3-indanediones and arylidenemalononitriles were employed in the reaction, the corresponding spiro[isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinoline-8,4′-pyrazole], spiro[indene-2,8′-isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinoline], and isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinoline derivatives were also prepared in good yields and with high diastereoselectivty. The relative configurations of the polycyclic spiro compounds were clearly elucidated by determination of fifteen single crystal structures.

Graphical abstract: Diastereoselective synthesis of spirocyclic isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinolines via cascade double [3 + 2]cycloadditions

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Publication details

The article was received on 02 Jul 2019, accepted on 07 Aug 2019 and first published on 07 Aug 2019


Article type: Paper
DOI: 10.1039/C9OB01474H
Org. Biomol. Chem., 2019, Advance Article

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    Diastereoselective synthesis of spirocyclic isoxazolo[5,4-c]pyrrolo[2,1-a]isoquinolines via cascade double [3 + 2]cycloadditions

    D. Liu, J. Sun, Y. Zhang and C. Yan, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01474H

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