8-Dihydro-3-methyl-7-amino-[1,2,4]triazino[3,4-b][1,3,4]thiadiazine
Majid M. Heravi a,c, Ghadir Rajabzadeh a, Mohammad Rahimizadeh a, Mehdi Bakavoli a and Mitra Ghassemzadeh b
a Department of Chemistry, School
of Sciences, Ferdowsi University of Mashhad, Iran. Department of Chemistry
b Chemistry & Chemical
Engineering Research Center of Iran, P.O.Box 14335-186, Tehran, Iran.
c Present address : School
of Sciences, Azzahra University, Vanak, Tehran, Iran (E-mail: [email protected]
Received: 23 October 2000 / Accepted: 30 November 2000 / Published: 25 December 2000
8-Dihydro-3-methyl-7-amino-[1,2,4]triazino[3,4-b][1,3,4]thiadiazine 2 was prepared by the cyclocondensation of 4-amino-6-methyl-3-thio-1,2,4-triazin-5-one 1 with chloro-acetonitrile in the presence of triethylamine in refluxing CH3CN. Compound 1 (316 mg, 2 mmol) was dissolved in acetonitrile (8 mL) containing triethylamine (0.4 mL, excess). To this solution chloroacetonitrile (0.2 mL, excess) was added. The reaction mixture was refluxed for 5hrs. The solvent was removed and the residue was subjected to column chromatography using CHCl3: MeOH 97:3 to afford 24 mg (61%) of 2 as white crystals.
Mp.: 114-115°C.
1H-NMR (100 MHz, d6-DMSO): 2.2 (s, 3H, CH3), 5.45 (s, 2H, CH2), 6.54 (s, 2H, NH2, exchangeable with D2O).
MS: 196 (12), 195 (44), 194 (79), 193 (89), 86 (20), 72 (43), 70 (100), 45 (43).
IR (KBr disc): 3300, 3250, 1690, 1550, 1440, 910, 880.
Reference
1. Dornow, A.; Menzel, H.; Marx, P. Ber.1964, 2173.
Sample availability : Available from the authors and MDPI.
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