Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides

Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2020, Volume: 56, Number: 12, Pages: 1569-1578 Pages count : 10 DOI: 10.1007/s10593-020-02851-w

Authors

Izmest’ev Alexei N. ^1,2 , Gazieva Galina A. ¹ , Kolotyrkina Natalya G. ¹ , Daeva Elena D. ¹ , Kravchenko Angelina N. ^1,3

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
2	National University of Science and Technology (MISiS), Moscow, Russia
3	Plekhanov Russian University of Economics, Moscow, Russia

Cleavage of 1,3-dimethyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-2,7(1H,6H)-diones upon treatment with aromatic aldehydes has been shown to afford (Z)-5-arylmethylidene-3-((E)-arylmethylideneamino)thiazolidine-2,4-diones bearing two identical or different arylmethylidene fragments at the exocyclic nitrogen atom and at position 5 of thiazolidine cycle. 1,3-Dipolar cycloaddition reaction of thiazolidine-2,4-dione derivatives with azomethine ylide generated from isatin and sarcosine gave diastereomerically pure dispiro[indole-3,2′-pyrrolidine-3′,5″-thiazolidine]-2,2″,4″-triones in good yields. Dispiro compound with two 4-methoxyphenyl fragments exhibited slight antiproliferative activity toward CCRF-CEM (leukemia) and CAKI-1 (renal cancer) cell lines.

Izmest’ev A.N. , Gazieva G.A. , Kolotyrkina N.G. , Daeva E.D. , Kravchenko A.N.
Synthesis of 5-arylmethylidene-3-(arylmethylideneamino)thiazolidine-2,4-diones via triazine ring cleavage of tetrahydroimidazothiazolotriazinediones and their reactions with azomethine ylides
Chemistry of Heterocyclic Compounds. 2020. V.56. N12. P.1569-1578. DOI: 10.1007/s10593-020-02851-w WOS Scopus OpenAlex

≡ Web of science:	WOS:000604795400013
≡ Scopus:	2-s2.0-85098887192
≡ OpenAlex:	W3119896176