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3-Nitropyridin-2-yl hydrazone of 5-Acetyl-3-phenyl-1,2,4-triazine
Open AccessShort Note

Semicarbazone and Thiosemicarbazone of 5-acetyl-3-(methylsulfanyl)-1,2,4-triazine

Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland
Molbank 2005, 2005(4), M434; https://doi.org/10.3390/M434
Received: 11 May 2004 / Accepted: 30 May 2004 / Published: 1 October 2005
Keywords: semicarbazone; thiosemicarbazone; 5-acetyl-1; 2; 4-triazine semicarbazone; thiosemicarbazone; 5-acetyl-1; 2; 4-triazine
Semicarbazone as well as thiosemicarbazone of 5-acetyl-3-(methylsulfanyl)-1,2,4-triazine were synthesised as reactive intermediates for the synthesis of 1H-pyrazolo[4,3-e][1,2,4]triazine derivatives via acid promoted ring closure [1,2,3].
Molbank 2005 m434 i001
Starting ketone 1 was prepared according to a reported procedure [4]. To a solution of ketone 1 (169 mg, 1 mmol) and semicarbazone or thiosemicarbazone (1.2 mmol) in ethanol (20 ml) 10% HCl (0.5 ml) was added. The resulting reaction mixture was heated at reflux for 5 min and then stirred at room temperature for additional 30 min. The precipitated solid was filtered off, recrystallized from dioxane and dried under vacuum.

Semicarbazone of 5-acetyl-3-(methylsulfanyl)-1,2,4-triazine (2)

Yield 89%.
Melting Point: 260ºC.
1H-NMR (200 MHz, DMSO-d6): δ= 2.19 (s, 3H); 2.62 (s, 3H); 6.96 (s, 2H, NH2); 9.98 (s, 1H); 10.13 (s, 1H, NH).
IR (CHCl3 film, cm-1): 3339; 3106; 1693; 1520; 1486; 1426; 1312; 1256; 1183; 1133; 1058; 871; 713.
MS- EI (m/z, %): 226 (18) [M+]; 209 (7); 184 (11); 183 (100); 182 (62); 155 (12); 154 (39); 140 (32); 82 (49); 81 (30); 74 (18); 53 (19).
HR-MS: Calculated for C7H10N6OS: 226.0636. Found: 226.06314.

Thiosemicarbazone of 5-acetyl-3-(methylsulfanyl)-1,2,4-triazine (3)

Yield 87%.
Melting Point: 229ºC.
IR (CHCl3 film, cm-1): 3304; 3158; 2969; 1587; 1495; 1423; 1243; 1127; 1057; 876.
1H-NMR (200 MHz, DMSO-d6): δ= 2.31 (s, 3H); 2.63 (s, 3H); 8.53 (s, 1H); 8.70 (s, 1H); 10.08 (s, 1H); 10.81 (s, 1H).
MS-EI (m/z, %): 242 (80) [M+]; 199 (21); 167 (7); 154 (6); 141 (5); 140 (22); 128 (27); 116 (100); 82 (12); 81 (12); 74 (14); 60 (24); 53 (13).
HR-MS: Calculated for C7H10N6S2: 242.04084; Found: 242.04129.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

References

  1. Rykowski, A.; Mojzych, M.; Karczmarzyk, Z. Heterocycles 2000, 53, 2175. [CrossRef]
  2. Mojzych, M.; Rykowski, A. Polish J. Chem. 2003, 77, 1797.
  3. Mojzych, M.; Rykowski, A. Heterocycles 2004. submitted.
  4. Rykowski, A.; Lipińska, T. Synth. Comm. 1996, 26, 4409. [CrossRef]
  • Sample Availability: Available from MDPI.
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