Stereoselective synthesis of dispiroindano pyrrolidines by the [3 + 2] cycloaddition of thiazolo[3,2‐a]indole tethered dipolarophile with azomethine ylides

Azomethine ylides generated by the reaction of cyclic ketones, namely ninhydrin, acenaphthene quinone and 11H‐indeno[1,2‐b]‐quinoxalin‐11‐one, with (i) α‐amino acids (ii) primary/secondary amines, have been successfully utilized for one‐pot three‐component [3 + 2] cycloaddition reactions with a thia...

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Veröffentlicht in:Journal of heterocyclic chemistry 2022-08, Vol.59 (8), p.1407-1416
Hauptverfasser: Thomas, Noble V., Sathi, Vidya, Deepthi, Ani
Format: Artikel
Sprache:eng
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Zusammenfassung:Azomethine ylides generated by the reaction of cyclic ketones, namely ninhydrin, acenaphthene quinone and 11H‐indeno[1,2‐b]‐quinoxalin‐11‐one, with (i) α‐amino acids (ii) primary/secondary amines, have been successfully utilized for one‐pot three‐component [3 + 2] cycloaddition reactions with a thiazolo[3,2‐a]indole containing dipolarophile (in‐turn generated by the reaction of thieno[2,3‐b]indole‐2,3‐dione and dimethyl acetylene dicarboxylate). Dispiro heterocycles were synthesized in excellent yields and with high stereo‐ and regioselectivity. Eco‐friendly synthesis of dispiro indanones by [3 + 2] cycloaddition of azomethine ylides with thiazolo[3,2‐a]indole tethered dipolarophile.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4481