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Volume 2005
Issue 2
10.3390/M414
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Short Note

Synthesis of N-Isopropylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine and N-Benzylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine

by
Mariusz Mojzych
Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland
Molbank 2005, 2005(2), M414; https://doi.org/10.3390/M414
Submission received: 23 April 2004 / Accepted: 30 July 2004 / Published: 1 August 2005
Versions Notes

As part of our ongoing research program on bicyclic heteroaromatics chemistry [1,2,3,4] we synthesised the title compounds with the goal of performing structure-activity relationship studies.
Molbank 2005 m414 i001

N-Isopropylidene-N’-(3-methyl-1-phenyl-1H-pyrazolo[4,3-e][1,2,4]triazin-5-yl)-hydrazine (2)

5-Hydrazino-1H-pyrazolo[4,3-e][1,2,4]triazine 1 (120 mg, 0.5 mmol) was dissolved in 20 ml of acetone. The mixture was stirred at room temperature for 10 min. The precipitated solid was filtered off and recrystallized from ethanol to give 2 (126 mg, 0.45 mmol) in 90% yield.
Melting Point: 165 °C.
1H-NMR (200 MHz, CDCl3): δ= 2.08 (s, 3H); 2.21 (s, 3H); 2.71 (s, 3H); 7.27-7.36 (m, 1H); 7.49-7.58 (m, 2H); 8.28-8.33 (m, 2H); 8.62 (s, 1H, NH).
13C-NMR (50 MHz, CDCl3): δ= 11.27; 16.53; 25.65; 119.41; 125.99; 129.27; 136.74; 138.73; 141.93; 146.87; 151.65; 158.65.
IR (KBr, cm-1): 3378; 2997; 1505.
MS (EI, 70eV; m/z, %): 281 (12) [M+]; 266 (100); 226 (15); 129 (18); 104 (26); 94 (14); 77 (51).
HR-MS (EI, 70eV): Calcd. for C14H15N7: 281.13889; Found: 281.13832.

N-Benzylidene-N’-(3-methyl-1-phenyl-1H-pyrazolo[4,3-e][1,2,4]triazin-5-yl)-hydrazine (3)

To a solution of 1 (120 mg, 0.5 mmol) in methanol (30 ml) benzaldehyde (0.1 ml, 1 mmol) and 10% HCl (0.3 ml) were added. The mixture was refluxed for 5 min and then stirred at room temperature for 30 min. The solvent was removed in vacuo and the crude product was recrystallized from dioxane. Yield of 3 is 88% (145 mg, 0.44 mmol).
Melting Point: 283 °C.
1H-NMR (200 MHz, DMSO): δ= 2.62 (s, 3H); 7.33-7.51 (m, 4H); 7.58-7.65 (m, 2H); 7.72-7.77 (m, 2H); 8.22 (s, 1H); 8.25-8.29 (m, 2H); 12.11 (s, 1H);
IR (KBr, cm-1): 3220; 1600; 1490; 750; 700.
HR-MS (ESI): Calcd for C18H16N7: 330.1462; Found: 330.1458.
Elemental Analysis: Calculated for C18H16N7.0.25H2O: C, 64.76%; H, 4.64%; N, 29.38%. Found: C, 64.82%, H, 4.68%; N, 29.38%.

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.
  2. Karczmarzyk, Z.; Mojzych, M.; Rykowski, A. J. Chem. Cryst. 2000, 30, 423.
  3. Mojzych, M.; Rykowski, A. Polish J. Chem. 2003, 77, 1797.
  4. Mojzych, M.; Rykowski, A. Heterocycles 2004. submitted.
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Mojzych, M. Synthesis of N-Isopropylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine and N-Benzylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine. Molbank 2005, 2005, M414. https://doi.org/10.3390/M414

AMA Style

Mojzych M. Synthesis of N-Isopropylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine and N-Benzylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine. Molbank. 2005; 2005(2):M414. https://doi.org/10.3390/M414

Chicago/Turabian Style

Mojzych, Mariusz. 2005. "Synthesis of N-Isopropylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine and N-Benzylidene-N’-(3-Methyl-1-Phenyl-1H-Pyrazolo[4,3-e][1,2,4]Triazin-5-yl)-Hydrazine" Molbank 2005, no. 2: M414. https://doi.org/10.3390/M414

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