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9-Methyl-3-phenyl-4H,6H--[1,2,4]triazino[5,4-b][1,3,4]thiadiazin-6-one

1
Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Iran
2
Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
3
Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M237; https://doi.org/10.3390/M237
Submission received: 17 December 2000 / Accepted: 15 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 06 m237 i001
4-Amino-6-methyl-5-thio-1,2,4-triazin-3-one 1 was reacted with phenacyl bromide in the presence of triethylamine in acetonitrile to give the corresponding 5-phenacylthio derivative 2. The latter was refluxed in aqueous solution of sodium carbonate to afford a novel heterocyclic system 3 (Scheme). Compound 1 (0.316 g, 2 mmol) was dissolved in a solution of CH3CN (10 mL) and triethylamine (2 mL). To this solution phenacyl bromide (0.4 g, 2 mmol) was added. The reaction mixture was stirred at room temperature for 5 hrs. The solvent was evaporated to dryness and the residue was crystallized from methanol to afford 2. Compound 2 was refluxed in a solution of sodium carbonate (0.5 g in water (6 mL)) for 2 hrs. The solution was neutralized by addition of 2N HCl and extracted with CHCl3. The solvent was evaporated to dryness and the residue was directly subjected to column chromatography (CHCl3:MeOH; 98:2) to afford 3.
Selected Data for 2. Yield: 71%, mp.: 202-3 °C, 1HNMR (DMSO, d6) d, 2.3(s, 3H, Me), 5.6(s, 2H, NH2, exchangeable with D2O), 7.6 and 8.8 (m, 5H, Ph). IR, (KBr disc): 3400, 3350, 1690, 1580, 1400, 1210 cm−1, M.S., m/z, M+, 276(65), 275(8), 105(58.5), 104(100), 103(63), 89(70), 80(74), 77(63).
Selected Data for 3. Yield: 50%, mp.: 230-2 °C, 1HNMR (DMSO, d6) d, 2.3(s, 3H, Me), 5.3(s, 2H, NH, exchangeable with D2O), 5.4 (s, 1H, =CH), 7.2-8.3(m, 5H, Ph). IR, (KBr disc): 3490, 1690, 1410, 800 cm−1, M.S., m/z, M+, 258(3), 255(11), 103(100), 71(44), 42(41).

References

  1. Heravi, M.M.; Rajabzadeh, Gh.; Rahimizadeh, M.; Bakavoli, M.; Ghassemzadeh, M. P, S, Si and Related Elements. 2000. submitted. [Google Scholar]
Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Heravi, M.M.; Rajabzadeh, G.; Rahimizadeh, M.; Bakavoli, M.; Ghassemzadeh, M. 9-Methyl-3-phenyl-4H,6H--[1,2,4]triazino[5,4-b][1,3,4]thiadiazin-6-one. Molecules 2001, 6, M237. https://doi.org/10.3390/M237

AMA Style

Heravi MM, Rajabzadeh G, Rahimizadeh M, Bakavoli M, Ghassemzadeh M. 9-Methyl-3-phenyl-4H,6H--[1,2,4]triazino[5,4-b][1,3,4]thiadiazin-6-one. Molecules. 2001; 6(12):M237. https://doi.org/10.3390/M237

Chicago/Turabian Style

Heravi, Majid M., Ghadir Rajabzadeh, Mohammad Rahimizadeh, Mehdi Bakavoli, and Mitra Ghassemzadeh. 2001. "9-Methyl-3-phenyl-4H,6H--[1,2,4]triazino[5,4-b][1,3,4]thiadiazin-6-one" Molecules 6, no. 12: M237. https://doi.org/10.3390/M237

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