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Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine Full article

Journal Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Output data Year: 2025, Volume: 184, Article number : 134782, Pages count : DOI: 10.1016/j.tet.2025.134782
Authors Izmest'ev Alexei N. 1 , Isakov Sergey S. 2,1 , Strelenko Yuri A. 1 , Kravchenko Angelina N. 1 , Gazieva Galina A. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2 D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russian Federation

Abstract: Four series of dispiro-fused polyheterocyclic compounds containing spiro(pyrrolidine-2,3′-oxindole) and imidazothiazolotriazine moieties were prepared by [3 + 2] cycloaddition of azomethine ylide to ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine. It was shown that ylide cycloaddition occurs to both diastereotopic faces of the dipolarophiles to give the target compounds as two diastereomers. Skeletal rearrangement of the major dispiro(imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidin-2′,3″-oxindoles) (anti-exo-diastereomers) gave isomeric dispiro(imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3′-pyrrolidin-2′,3″-oxindoles) (angular syn-exo-diastereomers) that are inaccessible by the direct [3 + 2] cycloaddition reaction.
Cite: Izmest'ev A.N. , Isakov S.S. , Strelenko Y.A. , Kravchenko A.N. , Gazieva G.A.
Diastereodivergent synthesis of novel dispiro(imidazothiazolotriazine-pyrrolidin-oxindoles) based on ortho- and meta-nitrobenzylidene derivatives of imidazothiazolotriazine
Tetrahedron. 2025. V.184. 134782 . DOI: 10.1016/j.tet.2025.134782 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:001518606900006
≡ Scopus: 2-s2.0-105008019335
≡ OpenAlex: W4411306643
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