All Title Author
Keywords Abstract

Publish in OALib Journal
ISSN: 2333-9721
APC: Only $99


Benzoylacetone as a Building Block in Heterocyclic Synthesis: Synthesis of Polyfunctionally Substituted Pyridinethione and Its Derivatives

DOI: 10.4236/oalib.1101274, PP. 1-9

Subject Areas: Analytical Chemistry, Organic Chemistry

Keywords: Pyridines, Pyrimidines, Pyridinthione, Pyridothienopyrimidine and Isoquinolines

Full-Text   Cite this paper   Add to My Lib


The Hantzsch amide derivatives 1 are prepared by reaction of a mixture of two moles of benzoylacetone, aqueous ammonia and aromatic aldehydes. Also, the reaction of benzoylacetone with a mixture of urea or thiourea and aromatic aldehydes afforded pyrimidine derivatives 2a-h. Pyridinethione derivative 3 was reacted with α–haloketones and α–halonitriles 4a-e to afford the S-alky- lated derivatives 5a-e which cyclized into 6b-e and 7. Reactions of compound 7 with glacial acetic acid/acetic anhydride gave 8 which led to 9a and 9b on treatment with ammonium acetate/acetic acid and aniline. Also, treatment of 7 with formamide, hydrazine hydrate and benzoyl isothiocyanate afforded 10, 11 and 13. Reactions of 3 with arylidenemalononitrile 14 in ethanolic triethylamine yielded 1:1 addact 17a-c.

Cite this paper

Hussein, A. H. M. , Abu-Shanab, F. A. and Mousa, S. A. H. S. (2015). Benzoylacetone as a Building Block in Heterocyclic Synthesis: Synthesis of Polyfunctionally Substituted Pyridinethione and Its Derivatives. Open Access Library Journal, 2, e1274. doi:


[1]  Sircar, I., Gregor, E.K., Anderson, K.R., Haleen, S.J., Shih, Y.H., Weishaar, R.E., Steffen, R.P., Pugsly, T.A. and Taylor, M.D. (1991) Calcium Channel Blocking and Positive Inotropic Activities of Ethyl 5-Cyano-1,4-Dihydro-6-Me- thyl-2-[(Phenylsulfonyl)Methyl]-4-Aryl-3-Pyridinecarboxylate and Analogs. Synthesis and Structure-Activity Relationships. Journal of Medicinal Chemistry, 34, 2248.
[2]  Shraideh, Z. and Salla, A.K. (1997) Biomedical Letters, 54, 233.
[3]  Gilis, P.M., Haemera, A. and Bollaert, W. (1980) European Journal of Medicinal Chemistry, 15, 185.
[4]  Bompart, J., Giral, I., Malicone, G. and Puygrenier, M. (1987) Synthesis and Anti-Bacterial Activities of New 4,7-Di- hydro 7-Ethyl 4-Oxo (2,3-b)Thieno Pyridine 5-Carboxylic Acids. European Journal of Medicinal Chemistry, 22, 139- 145.
[5]  Abdel-Rahman, A.E., Bakhite, E.A. and Al-Taifi, E.A. (2002) Journal of the Chinese Chemical Society, 49, 223.
[6]  Attaby, F.A., Elneairy, M.A.A. and Elsayed, M.S. (1999) Synthesis and Antimicrobial Evaluation of Several New Pyridine, Thienopyridine and Pyridothienopyrazole Derivatives. Phosphorus, Slfur and Silicon, 149, 49-64.
[7]  Eldin, S.M. (1999) Zeitschrift für Naturforschung, 45b, 674.
[8]  Adachi, I. and Hiramatsu, Y. (1991) 4,7-Dihydro-5-Alkoxycarbonyl-6-Methyl-4-(Nitrophenyl)Thieno[2,3-b]Pyridine- 2-Carboxylic Acids as Intermediates for Calcium Channel Blockers. Chemical Abstracts, 115, 71573.
[9]  Hussein, A.M. (1998) Zeitschrift für Naturforschung, 53b, 1.
[10]  Hussein, A.M., Shrief, S.M. and Atalla, A.A. (1996) A New Synthesis for 1,2,4-Triazolo[1,5-a]-Pyridines and 1,2,4- Triazolo[1,5-a]Isoquinolines. Monatshefte für Chemie, 127, 1153-1160.
[11]  Gelbard, G., Lin, J. and Roques, N. (1992) Reductions with NADH Models. 3. The High Reactivity of Hantzsch Amides. Journal of Organic Chemistry, 57, 1789-1793.
[12]  Vieweg, H., Leistner, S. and Wagner, G. (1986) Pharmazie, 41, 827.
[13]  Hussein, A.M. (1997) Studies with Polyfunctionally Substituted Heteroaromatics: A Facile Route for the Synthesis of Polyfunctionally Substituted N-Aminopyridines, 1,2,4-Triazolo[1,5-a]Pyridines and Isoquinolines. Heteroatom Chemistry, 8, 1.<1::AID-HC1>3.0.CO;2-J


comments powered by Disqus

Contact Us


微信:OALib Journal