Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide | Zendy

RongGuo Shi | Zendy; Jing Sun | Zendy; ChaoGuo Yan | Zendy

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Tandem Double [3 + 2] Cycloaddition Reactions at Both C-1 and C-3 Atoms of N-Cyanomethylisoquinolinium Ylide

Author(s) -

RongGuo Shi,

Jing Sun,

ChaoGuo Yan

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01391

Subject(s) - cycloaddition , chemistry , triethylamine , medicinal chemistry , tandem , ylide , tetrahydrofuran , acetonitrile , indene , isoquinoline , chloride , base (topology) , nitrile , organic chemistry , catalysis , solvent , materials science , composite material , mathematical analysis , mathematics

The base-promoted cycloaddition reaction of N -cyanomethylisoquinolinium chloride with 2-arylidene-1,3-indanediones in dry tetrahydrofuran resulted in the expected spiro[indene-2,1'-pyrrolo[2,1- a ]isoquinoline] derivatives. However, the triethylamine-promoted three-component reaction of N -cyanomethylisoquinolinium chloride, aromatic aldehydes, and two molecules of 1,3-indanediones in acetonitrile afforded unique spiro[benzo[ f ]imidazo[5,1,2- cd ]indolizine-4,2'-indene] derivatives in satisfactory yields through tandem double [3 + 2] cycloaddition reactions.

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