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Volume 2005
Issue 2
10.3390/M413
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Short Note

A Rapid Synthesis of the 3-Methyl-5-(Methylsulfanyl)-1-Phenyl-1H-Pyrazolo[4,3-e]-[1,2,4]Triazine from Phenylhydrazone of 5-Acetyl-3-(Methylsulfanyl)-1,2,4-Triazine under Microwave Irradiation

by
Mariusz Mojzych
Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland
Molbank 2005, 2005(2), M413; https://doi.org/10.3390/M413
Submission received: 24 March 2004 / Accepted: 29 April 2004 / Published: 1 August 2005
Versions Notes

The combination of microwave irradiation and solvent-free conditions leads to enhanced reaction rates, higher yields of pure products, easier work-up and several advantages of the eco-friendly approach in the framework of green-chemistry [1,2]. Here we report a new route for the preparation of 1H-pyrazolo[4,3-e][1,2,4]triazine derivative 2 starting from phenylhydrazone of 5-acetyl-3-(methylsulfanyl)-1,2,4-triazine (1) [3] and p-toluenesulfonic acid (p-TsOH) under microwave irradiation.
Molbank 2005 m413 i001
The mixture of the phenylhydrazone 1 (259 mg, 1mmol) and p-toluenesulfonic acid (344 mg, 2 mmol) was heated in quartz container under microwave irradiation [4]. After 2 min the product was eluted with CHCl3. The crude product 2 was purified by column chromatography on silica gel (Merck, 230-400 mesh) using chloroform as eluent. Yield of pure 3-methyl-5-(methylsulfanyl)-1-phenyl-1H-pyrazolo[4,3-e][1,2,4]triazine (2) – 149 mg (0.58 mmol, 58%).
Melting Point: 105 oC.
1H-NMR (200 MHz, CDCl3): δ= 2.73 (s, 3H); 2.77 (s, 3H); 7.29-7.40 (m, 1H); 7.50-7.61 (m, 2H); 8.31-8.38 (m, 2H).
IR (KBr, cm-1): 2920, 1590, 1500, 1390, 760.
MS (EI, 70eV; m/z, %): 257 (43) [M+]; 232 (3); 216 (22); 93 (41); 77 (100).
Elemental Analysis: Calculated for C12H11N5S: C, 56.03%; H, 4.28%; N, 27.23%. Found: C, 55.67%; H, 4.13%; N, 27.05%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
  2. Varma, R.S. Green Chem. 1999, 1, 43.
  3. Rykowski, A.; Mojzych, M.; Karczmarzyk, K. Heterocycles 2000, 53, 2175.
  4. The Prolabo microwave synthesizer SYNTHEWAVE 402 was used with feedback temperature control.
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Mojzych, M. A Rapid Synthesis of the 3-Methyl-5-(Methylsulfanyl)-1-Phenyl-1H-Pyrazolo[4,3-e]-[1,2,4]Triazine from Phenylhydrazone of 5-Acetyl-3-(Methylsulfanyl)-1,2,4-Triazine under Microwave Irradiation. Molbank 2005, 2005, M413. https://doi.org/10.3390/M413

AMA Style

Mojzych M. A Rapid Synthesis of the 3-Methyl-5-(Methylsulfanyl)-1-Phenyl-1H-Pyrazolo[4,3-e]-[1,2,4]Triazine from Phenylhydrazone of 5-Acetyl-3-(Methylsulfanyl)-1,2,4-Triazine under Microwave Irradiation. Molbank. 2005; 2005(2):M413. https://doi.org/10.3390/M413

Chicago/Turabian Style

Mojzych, Mariusz. 2005. "A Rapid Synthesis of the 3-Methyl-5-(Methylsulfanyl)-1-Phenyl-1H-Pyrazolo[4,3-e]-[1,2,4]Triazine from Phenylhydrazone of 5-Acetyl-3-(Methylsulfanyl)-1,2,4-Triazine under Microwave Irradiation" Molbank 2005, no. 2: M413. https://doi.org/10.3390/M413

APA Style

Mojzych, M. (2005). A Rapid Synthesis of the 3-Methyl-5-(Methylsulfanyl)-1-Phenyl-1H-Pyrazolo[4,3-e]-[1,2,4]Triazine from Phenylhydrazone of 5-Acetyl-3-(Methylsulfanyl)-1,2,4-Triazine under Microwave Irradiation. Molbank, 2005(2), M413. https://doi.org/10.3390/M413

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