Synthesis of Enol ether,α,β-unsaturated carbonyl compound, Oxoketenedithio acetal and Dimethyl aminomethylene ketone derivatives of s-Triazines as Intermediates for Synthesis of Fused Heterocycles

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Synthesis of Enol ether,α,β-unsaturated carbonyl compound, Oxoketenedithio acetal and Dimethyl aminomethylene ketone derivatives of s-Triazines as Intermediates for Synthesis of Fused Heterocycles

Author Affiliations

¹Department of Chemistry, Banasthali Vidyapith, Banasthali, Rajasthan, 304 022, INDIA
² Department of Pure and Applied Chemistry, University of Kota, Rajasthan, 324 005, INDIA

Res.J.chem.sci., Volume 5, Issue (11), Pages 9-12, November,18 (2015)

Abstract

The synthesis of enol-ether, αβ-unsaturated carbonyl compound,oxoketenedithio acetaland dimethyl aminomethylene ketonederivatives of quinazoline and pyrimidine containing trisubstituted s-triazines. Apart from this, quinazoline and pyrimidine containing trisubstituted s-triazine template has also been used to synthesize quinoline-4-carboxylic acid moiety and diazepinone derivatives by adopting the Pfitzinger reaction and Beckmannrearrangement methodology. The structures of all the compounds have been confirmed by elemental analysis and spectral data.

References

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Bonacorso H.G., Wastowski A.D., Zanatta N., Martins M.A.P. and Naue J.A., Haloacetylated enol ethers 10. Condensation of b-alkoxyvinyl tri-uoromethyl ketones with thiosemicarbazide. Synthesis of new tri-uoromethyl 4,5-dihydro-1H-1 pyrazolethiocarboxyamides, J. Fluorine Chem.,92, 23-26 (1998)
In J.K., Lee M.S., Lee M.W., Kwak J.H., Lee H., Hong J.T., Chung Y., Choi Y. and Jung J.K., Stereoselective synthesis of (E)- and (Z)-enol ethers from -amino aldehydes, Arch. Pharm. Res.,30(6), 695-700 (2007)
Juan R., Legros, J. and Bolm C., Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions, Chem. Commun., 973-986 (2005)
Patil C.B., Mahajan S.K. and Katti S.A., Chalcone: A versatile molecule, J. Pharm. Sci. Res., l1(3), 11-22 (2009)
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Mehta B.K., Nandi S., lla H. and Junjappa H, Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to -oxoketene dithioacetals: A facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation, Tetrahedron,55, 12843-12852 (1999)
Chen H.S., Li Z.M. and Wang Z.W., A convenient synthesis of pyrazolylpyrazoles using -oxoketene S,S- and N,S-acetals, Chinese Chem. Lett.,10(8), 643–646 (1999)
Zhao M.X., Liu Q., Hu Y.L. and Li D.L., -Oxoketene dithioacetals chemistry-A facile route to the synthesis of fused heterocyclic compounds, Chinese Chem. Lett., 11(4), 283-284 (2000)
Hassneen H.M.and Abdallah T.A., New routes to pyridino[2,3-d]pyrimidin-4-one and pyridino-[2,3-d] triazolino [4,5-a] pyrimidin-5-one derivatives, Molecules,8, 333-341 (2003)
Jiang J.L, Ju J. and Hua R., A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1,2-disubstituted-3,4-dihydronaphthalenes catalysed by dimethylformamide dimethyl acetal, Org. Biomol. Chem., 5, 1854-1857 (2007)
Dzhavakhishvili S.G., Gorobets N.Y., Chernenko V.N., Musatov V.I. and Desenko S.M., Synthesis of novel 3(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones, Russian Chem. Bull., 57(2), 422-427 (2008)
Wang D.L., Gu Z., Xu J., Han S. and Imafuku K., New synthetic approach to 4-N-arylaminoazuleno[2,1-d]pyrimides, Synthetic Commun.,39, 2329-2338 (2009)
Shekhawat S., Sharma A., Kishore D. and Singh B., Synthesis of trisubstituted s-triazine templates to prepare some reactive intermediates for the synthesis of medicinally potent novel heterocycles, J. Chem. Chem. Sci.,5(9), 517-521 (2015)

[ref1] Katritzky A.R., Bayyuk S.I. and Rachwal S., An efficient synthesis of ketone enol ethers mediated by N-(1-Alkoxyalyl) benzonitriles, Synthesis, 279-283 (1991)

[ref2] Bonacorso H.G., Wastowski A.D., Zanatta N., Martins M.A.P. and Naue J.A., Haloacetylated enol ethers 10. Condensation of b-alkoxyvinyl tri-uoromethyl ketones with thiosemicarbazide. Synthesis of new tri-uoromethyl 4,5-dihydro-1H-1 pyrazolethiocarboxyamides, J. Fluorine Chem.,92, 23-26 (1998)

[ref3] In J.K., Lee M.S., Lee M.W., Kwak J.H., Lee H., Hong J.T., Chung Y., Choi Y. and Jung J.K., Stereoselective synthesis of (E)- and (Z)-enol ethers from -amino aldehydes, Arch. Pharm. Res.,30(6), 695-700 (2007)

[ref4] Juan R., Legros, J. and Bolm C., Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions, Chem. Commun., 973-986 (2005)

[ref5] Patil C.B., Mahajan S.K. and Katti S.A., Chalcone: A versatile molecule, J. Pharm. Sci. Res., l1(3), 11-22 (2009)

[ref6] Baviskar B.A., Baviskar B., Shiradkar M.R., Deokate U.A. and Khadabadi S.S., Synthesis and antimicrobial activity of some novel benzimidazolyl chalcones, E-Journal Chem.,6(1), 196-200 (2009)

[ref7] Mu1ller T.J.J., Braun R. and Ansorge M., A novel three-component one-pot pyrimidine synthesis based upon a coupling-isomerization sequence, Org. Lett.,2(13), 1967-1970 (2000)

[ref8] Mathews A., Anabha E.R. and Sholly C.G., A facile method for the synthesis of oxoketene-N,S- and -N,Nacetals from reactions of amino compounds, Org. Chem.,1-5 (2010)

[ref9] Mehta B.K., Nandi S., lla H. and Junjappa H, Highly regioselective 1,2-addition of alkoxybenzyl Grignard reagents to -oxoketene dithioacetals: A facile regiocontrolled synthesis of alkoxynaphthalenes and their condensed analogs via aromatic annelation, Tetrahedron,55, 12843-12852 (1999)

[ref10] Chen H.S., Li Z.M. and Wang Z.W., A convenient synthesis of pyrazolylpyrazoles using -oxoketene S,S- and N,S-acetals, Chinese Chem. Lett.,10(8), 643–646 (1999)

[ref11] Zhao M.X., Liu Q., Hu Y.L. and Li D.L., -Oxoketene dithioacetals chemistry-A facile route to the synthesis of fused heterocyclic compounds, Chinese Chem. Lett., 11(4), 283-284 (2000)

[ref12] Hassneen H.M.and Abdallah T.A., New routes to pyridino[2,3-d]pyrimidin-4-one and pyridino-[2,3-d] triazolino [4,5-a] pyrimidin-5-one derivatives, Molecules,8, 333-341 (2003)

[ref13] Jiang J.L, Ju J. and Hua R., A highly efficient cycloaddition of vinylarenes with electron-deficient alkynes affording 1,2-disubstituted-3,4-dihydronaphthalenes catalysed by dimethylformamide dimethyl acetal, Org. Biomol. Chem., 5, 1854-1857 (2007)

[ref14] Dzhavakhishvili S.G., Gorobets N.Y., Chernenko V.N., Musatov V.I. and Desenko S.M., Synthesis of novel 3(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones, Russian Chem. Bull., 57(2), 422-427 (2008)

[ref15] Wang D.L., Gu Z., Xu J., Han S. and Imafuku K., New synthetic approach to 4-N-arylaminoazuleno[2,1-d]pyrimides, Synthetic Commun.,39, 2329-2338 (2009)

[ref16] Shekhawat S., Sharma A., Kishore D. and Singh B., Synthesis of trisubstituted s-triazine templates to prepare some reactive intermediates for the synthesis of medicinally potent novel heterocycles, J. Chem. Chem. Sci.,5(9), 517-521 (2015)