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Volume 2007
Issue 2
10.3390/M541
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Short Note

Efficient Synthesis of 6-Methyl-4-phenyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazine under Solvent-free Conditions

by
M. Raghavendra
,
Halehatty S. Bhojya Naik
*,
Tangali R. Ravikumar Naik
and
Bailure S. Sherigara
Department of PG Studies and Research in Industrial Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta- 577-451, Karnataka, India
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(2), M541; https://doi.org/10.3390/M541
Submission received: 11 January 2007 / Accepted: 16 January 2007 / Published: 31 May 2007
Versions Notes

Molbank 2007 m541 i001
In recent years reaction under solvent free conditions gaining much popularity because under solvent free conditions products obtains in high yield, avoids the use of hazardous and expensive solvents, and makes the manipulation much easier.
Tetrazoles and triazines posses wide class of biological activities [1,2,3,4,5,6]. It is known that fused tetrazoles can be prepared by employing Schmidt reaction of ketones with hydrazoic acid or inorganic azides [1], but inorganic azides are poorly soluble in organic solvent results increase in reaction time and decrease in yield. So, we wished to carry out above reaction under solvent media using anhydrous AlCl3 as catalyst.
Mixture of 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (0.696 g, 0.004 mol) 1, and Sodium azide (1.3 g, 0.020 mol) was ground portion-wise with anhydrous aluminium chloride (0.012 mol) taken in the mortor, continued the grinding for 20 min, During grinding considerable heat liberates which is sufficient to complete the reaction. After the completion of the reaction, reaction mixture was poured into water obtained solid was filtered, washed with water, recrystallised from aqueous DMF.
Melting Point: 151-152 oC
MS (m/z, %): 214 ([M+H]+, 100%).
IR (KBr, cm-1): 1525, 1480, 1425, and 1245 (tetrazole region), 1650 (C=N)
1H-NMR (400 MHz, DMSO-d6): 4.35 (2H, s, -CH2); 2.54 (3H, s, CH3); 6.90-7.10 (5H, ArH,).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Wittenberger, S. J. Org. Prep. Proced. Int. 1994, 26, 499.
  2. Butler, R.N. Comprehensive Heterocyclic Chemistry II; Storr, R. C., Ed.; Elsevier: Oxford, UK, 1996; Volume 4, p. 621. [Google Scholar]
  3. Juby, P.F.; Hudyma, T.W.; Brown, M. J. Med. Chem. 1968, 11, 111. [PubMed]
  4. Herbst, R.M.; Roberts, C.W.; Givens, H.T.F.; Harvill, E.K. J. Org. Chem. 1952, 17, 262.
  5. Segarra, V.; Crespo, M.I.; Pujol, F.; Beleta, J.; Domenech, T.; Miralpeix, M.; Palacios, J.M.; Castro, A.; Marinez, A. Bioorg. Med. Chem. Lett. 1998, 8, 505. [PubMed]
  6. O’Brien, P.M.; Sliskovich, D.R.; Bernabei, A.; Hurley, T.; Anderson, M.K.; Bousley, R.F.; Krause, B.R.; Stanfield, R.L. Bioorg. Med. Chem. Lett. 1995, 5, 295.
  7. Neunhoffer, H.; wiley, P. F. Chemistry of 1,2,3-triazines and 1,2,4-triazines, tetrazines and pentazines, Weissberger, A., Taylor, E. C., Eds.; 1978; J. Wiley and Sons New York, Brisbane, Toronto 1001.

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MDPI and ACS Style

Raghavendra, M.; Bhojya Naik, H.S.; Ravikumar Naik, T.R.; Sherigara, B.S. Efficient Synthesis of 6-Methyl-4-phenyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazine under Solvent-free Conditions. Molbank 2007, 2007, M541. https://doi.org/10.3390/M541

AMA Style

Raghavendra M, Bhojya Naik HS, Ravikumar Naik TR, Sherigara BS. Efficient Synthesis of 6-Methyl-4-phenyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazine under Solvent-free Conditions. Molbank. 2007; 2007(2):M541. https://doi.org/10.3390/M541

Chicago/Turabian Style

Raghavendra, M., Halehatty S. Bhojya Naik, Tangali R. Ravikumar Naik, and Bailure S. Sherigara. 2007. "Efficient Synthesis of 6-Methyl-4-phenyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazine under Solvent-free Conditions" Molbank 2007, no. 2: M541. https://doi.org/10.3390/M541

APA Style

Raghavendra, M., Bhojya Naik, H. S., Ravikumar Naik, T. R., & Sherigara, B. S. (2007). Efficient Synthesis of 6-Methyl-4-phenyl-4,7-dihydrotetrazolo[5,1-c][1,2,4]triazine under Solvent-free Conditions. Molbank, 2007(2), M541. https://doi.org/10.3390/M541

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