Diastereodivergent synthesis of dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties

Diastereodivergent synthesis of dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2020, Volume: 18, Number: 35, Pages: 6905-6911 Pages count : 7 DOI: 10.1039/d0ob01628d

Authors

Izmest'ev Alexei N. ¹ , Gazieva Galina A. ¹ , Karnoukhova Valentina A. ² , Kravchenko Angelina N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str., 28, Moscow 119991, Russian Federation

Highly diastereoselective methods for the synthesis of two different diastereomers of polynuclear dispiroheterocyclic compounds with five chiral centers comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties (dispiro[imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-7,3′-pyrrolidine-2′,3′′-indoles]) have been developed on the basis of a dipolar cycloaddition of azomethine ylides to benzylidene derivatives of imidazothiazolotriazines and an alkali-induced rearrangement of the thiazolotriazine fragment. The different sequence of the cycloaddition and rearrangement stages allows us to perform the targeted synthesis of two diastereomerically pure products from the same starting compounds.

Izmest'ev A.N. , Gazieva G.A. , Karnoukhova V.A. , Kravchenko A.N.
Diastereodivergent synthesis of dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties
Organic & Biomolecular Chemistry. 2020. V.18. N35. P.6905-6911. DOI: 10.1039/d0ob01628d WOS Scopus OpenAlex

≡ Web of science:	WOS:000571281400015
≡ Scopus:	2-s2.0-85091191665
≡ OpenAlex:	W3080733700