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Synthesis of A Novel Heterocyclic System of 3,8-Disubstituted-5H-Pyrimido[5’,4’:5,6][1,4]Thiazino[3,2-e][1,2,4]Triazine
Polycyclic Aromatic Compounds ( IF 2.4 ) Pub Date : 2020-06-26
Azam Karimian, Zahra Karimi

The new compounds 6-methyl-8-morpholino-2H pyrimido[5’,4’:5,6][1,4]thiazino[3,2e][1,2,4]triazin-3(5H)-one (3a) and 6-methyl-8-(piperidin-1-yl)-2Hpyrimido[5’,4’:5,6][1,4]thiazino[3,2-e][1,2,4]triazin-3(5H)-one (3b) were obtained from cyclocondensation of 6-bromo-1,2,4-triazine-3,5(2H,4H)-dione (1) with appropriate 5-amino-6methylpyrimidine-4-thiol (2a, b) in dimethylformamide and in the presence of potassium carbonate under reflux. Reaction of compounds (3a, b) with phosphorous oxychloride gave 4-(3-chloro-6-methyl-5H-pyrimido[5’,4’:5,6][1,4]thiazino[3,2-e][1,2,4]triazin-8-yl)morpholine (4a) and 3-chloro-6-methyl-8-(piperidin-1-yl)-5H-pyrimido[5’,4’:5,6][1,4]thiazino[3,2-e][1,2,4]triazine (4b). Nucleophilic substitution of chlorine atom of compounds (4a, b) with typical secondary amines in DMF and K2CO3 produced the new derivatives of the 3,8-disubstituted-5H-pyrimido[5’,4’:5,6][1,4]thiazino[3,2-e][1,2,4]triazine ring systems (5a–f). All the synthesized products were characterized and confirmed by their spectroscopic and microanalytical data.



中文翻译:

3,8-二取代-5H-嘧啶基[5',4':5,6] [1,4]噻嗪基[3,2-e] [1,2,4]三嗪杂环体系的合成

新化合物6-甲基-8-吗啉代2 H嘧啶[5',4':5,6] [1,4]噻嗪基[3,2 e ] [1,2,4]三嗪-3(5 H)- (3a)和6-甲基-8-(哌啶-1-基)-2 H嘧啶基[5',4':5,6] [1,4]噻嗪[3,2- e ] [1 1,2,4]三嗪-3(5 ħ) -酮(3b)中从6-溴-1,2,4-三嗪-3,5-环缩合的获得(2 ħ,4 ħ) -二酮(1)与在二甲基甲酰胺中,在碳酸钾存在下,在回流下,加入合适的5-氨基-6甲基嘧啶-4-硫醇(2a,b)。化合物(3a,b)的反应用三氯氧磷得到4-(3-氯-6-甲基-5 H-嘧啶基[5',4':5,6] [1,4]噻嗪[3,2- e ] [1,2,4]三嗪8-基)吗啉(4a)和3-氯-6-甲基-8-(哌啶-1-基)-5 H-嘧啶基[5',4':5,6] [1,4]噻嗪[3,2- e ] [1,2,4]三嗪(4b)。用DMF和K 2 CO 3中的典型仲胺对化合物(4a,b)的氯原子进行亲核取代,生成了3,8-二取代-5 H-嘧啶基的新衍生物[5',4':5,6] [1,4]噻嗪基[3,2- e ] [1,2,4]三嗪环系统(5a–f)。所有合成的产物均通过其光谱学和微观分析数据进行了表征和确认。

更新日期:2020-06-26
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