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Novel Synthesis and Characterization of Some Pyrimidine Derivatives of Oxadiazoles, Triazole and 1,3,4-Thiadiazoles
Corresponding Author(s) : B. Andrews
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
In the present investigation, synthetic methods of 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydro pyrimidine-(5)-1,3,4-thiadiazole-2-amine (3) and 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydro pyrimidine-(5)-1,3,4-oxadiazole-2-amine (3a) and 4-aryl-6-methyl-2-oxo-1,2,3,4-tetrahydro pyrimidine-(5)-1,3,4-triazole-2-thiol derivative (3b) are described. Compound 1 is converted to carbothiamide 2 by the reaction with ethyl ester followed by thiosemicarbazide. Compound 2 acts as key intermediate for all series of the final compounds. In one pathway, 2 is converted to corresponding thiadiazole 3 by treatment with conc. H2SO4 and NH3 and compound 3a by treatment with I2 followed by KI and NaOH and compound 3b by treatment with 10 % of NaOH to furnish the final compound. Structural elucidation is accomplished by IR, 1H NMR and mass spectral data of the synthesized compounds.
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- C.O. Kape, Tetrahedron, 49, 6937 (1993).
- C.O. Kape, Eur. J. Med. Chem., 35, 1043 (2000).
- A. Manjula, B.V. Rao and P. Neelakantam, Synth. Commun., 34, 2665 (2004).
- A.J. Zych, H.-J. Wang and S.A. Sakwa, Tetrahedron Lett., 51, 5103 (2010).
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- M.B. Moore and R.T. Rapela, J. Am. Chem. Soc., 68, 1657 (1946).
- R.O. Atkinson, J. Chem. Soc., 1329 (1954).
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- X. Zou and G. Jin, J. Heterocycl. Chem., 38, 993 (2001).
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- S.G. Jagadhani, S.B. Kale, N.R. Dalvi, M.S. More and B.K. Karale, Indian J. Heterocycl. Chem., 15, 335 (2006)
References
C.O. Kape, Tetrahedron, 49, 6937 (1993).
C.O. Kape, Eur. J. Med. Chem., 35, 1043 (2000).
A. Manjula, B.V. Rao and P. Neelakantam, Synth. Commun., 34, 2665 (2004).
A.J. Zych, H.-J. Wang and S.A. Sakwa, Tetrahedron Lett., 51, 5103 (2010).
Garima, V.P. Srivastava and L.D.S. Yadav, Tetrahedron Lett., 51, 6436 (2010).
M.B. Moore and R.T. Rapela, J. Am. Chem. Soc., 68, 1657 (1946).
R.O. Atkinson, J. Chem. Soc., 1329 (1954).
R.S. Varma, J. Indian Chem. Soc., 81, 627 (2004).
M. Kidwai, R. Venkataramanan and B. Dave, J. Heterocycl. Chem., 39, 1045 (2002).
N.A. Ross and R.A. Burtsch, J. Heterocycl. Chem., 38, 1255 (2001).
V. Singh, V. Sapehiyia and G.L. Kad, Synthesis, 198 (2003).
X. Zou and G. Jin, J. Heterocycl. Chem., 38, 993 (2001).
N.A. Ross and R.A. Burtsch, J. Heterocycl. Chem., 38, 1255 (2001).
S.G. Jagadhani, S.B. Kale, N.R. Dalvi, M.S. More and B.K. Karale, Indian J. Heterocycl. Chem., 15, 335 (2006)