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

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.

Automated summary

Treatment 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 with aromatic aldehydes results in the formation of (Z)-5-arylmethylidene-3-((E)-arylmethylideneamino)thiazolidine-2,4-diones. Additionally, 1,3-dipolar cycloaddition reaction of thiazolidine-2,4-dione derivatives yield diastereomerically pure dispiro[indole-3,2'-pyrrolidine-3',5''-thiazolidine]-2,2'',4''-triones with slight antiproliferative activity towards CCRF-CEM (leukemia) and CAKI-1 (renal cancer) cell lines.