Synthesis and Biological Evaluation of Some Novel N , N ′-Bis-(1,2,4-Triazin-4-Yl)Dicarboxylic Acid Amides and Some Fused Rings with 1,2,4-Triazine Ring

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 177; no. 3; pp. 587 - 596
• Main Authors: El-Badawi, M. A., El-Barbary, A. A., Lokshaa, Y. M., El-Daly, Mai
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis Group 01.03.2002; Taylor & Francis
• Subjects: 1,2,4-triazine; 1-Chloro-2,4-dinitrobenzene; 2,4-pentanedione; 2-bromopropionyl Bromide; 3,1-benzoxazin-4 H -ones; Anti-HBV Activity; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Dicarboxylic Acids; Physical Sciences; Science & Technology; 2,4-pentanedione; 3,1-benzoxazin-4H-ones; 2-bromopropionyl bromide; 1-chloro-2,4-dinitrobenzene; anti-HBV activity; dicarboxylic acids; 1,2,4-triazine
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426500210276

Some of novel N , N '-bis-(1,2,4-triazin-4-yl)dicarboxylic acid amides ( 2-5 ) and thiadiazolo[2,3- b ][1,2,4]triazin-7-yl carboxylic acid derivatives ( 6 , 7 ) were prepared by heating 4-amino-6-methyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine ( 1 ) with different dicarboxylic acids (oxalic, malonic, fumaric, maleic, succinic, and phthalic acids respectively) in POCl 3 . Refluxing 1 with 1-chloro-2,4-dinitrobenzene in DMF yielded 3-methyl-6-nitro-10 H -benzo[1,2,4]thiadiazino[2,3- c ][1,2,4]triazin-4-one ( 8 ). Condensation of 1 with 2,4-pentandione in refluxing acetic acid furnished 6-methyl-4-(1-methyl-3-oxobut-1-enylamino)-3-thioxo-3,4-dihydro-2 H -[1,2,4]triazin-5-one ( 9 ). 3,8-D imethyl[1,2,4] triazino[3,4- b ][1,3,4]thiadiazine-4,7-dione ( 11 ) was prepared by refluxing 1 with 2-bromopropionyl bromide in anhydrous benzene to afford the corresponding N -acetylated derivative 10 , which was cyclized by using triethylamine. Also, some triazinylquinazolinones 13a , b were obtained by fusion of 1 with 6-bromo(and/or 6,8-dibromo)-2-methyl-3,1-benzoxazin-4 H -ones.