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

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 56; no. 12; pp. 1569 - 1578
• Main Authors: Izmest’ev, Alexei N., Gazieva, Galina A., Kolotyrkina, Natalya G., Daeva, Elena D., Kravchenko, Angelina N.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-12-2020; Springer; Springer Nature B.V
• Subjects: Aldehydes; Chemistry; Chemistry and Materials Science; Cleavage; Cycloaddition; Diketones; Fragments; Leukemia; Nitrogen; Organic Chemistry; Pharmacy; Schiff bases; aldehydes; cleavage; spirooxindoles; thiazolidine-2,4-diones; cycloaddition; spiro compounds
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-020-02851-w

Cleavage of 1,3-dimethyl-3,3a,9,9a-tetrahydroimidazo[4,5-
e
]thiazolo[3,2-
b
][1,2,4]triazine-2,7(1
H
,6
H
)-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.