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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 ( IF 1.4 ) Pub Date : 2021-01-04 , DOI: 10.1007/s10593-020-02851-w
Alexei N. Izmest’ev , Galina A. Gazieva , Natalya G. Kolotyrkina , Elena D. Daeva , Angelina N. Kravchenko

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.



中文翻译:

通过四氢咪唑并噻唑并三唑二酮的三嗪环裂解合成5-芳基亚甲基-3-(芳基亚甲基氨基)噻唑烷-2,4-二酮及其与偶氮甲碱的反应

1,3-二甲基-3,3a,9,9a-四氢咪唑[4,5- e ]噻唑并[3,2- b ] [1,2,4]三嗪-2,7(1 H,6 H)-二酮经芳香族醛处理后显示可提供(Z)-5-芳基亚甲基-3-((E)-芳基亚甲基氨基)噻唑烷-2,4-二酮在环外氮原子和噻唑烷环的5位带有两个相同或不同的芳基亚甲基片段。噻唑烷-2,4-二酮衍生物与靛红和肌氨酸生成的偶氮甲碱内酯的1,3-偶极环加成反应得到非对映体纯的二螺并[吲哚-3,2'-吡咯烷-3',5″-噻唑烷] -2,2 ″,4″-三酮类,收率高。具有两个4-甲氧基苯基片段的双螺化合物对CCRF-CEM(白血病)和CAKI-1(肾癌)细胞系表现出轻微的抗增殖活性。

更新日期:2021-01-04
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