Open Access Library Journal
How to 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. http://dx.doi.org/10.4236/oalib.1101274
Benzoylacetone as a Building Block in
Heterocyclic Synthesis: Synthesis of
Polyfunctionally Substituted
Pyridinethione and Its Derivatives
Abdel Haleem Mostafa Hussein
*
, Fathi Ali Abu-Shanab, Sayed Abdel Hamed Sayed Mousa
Department of Chemistry, Faculty of Science, Al Azhar University, Assiut, Egypt
Email:
*
abdelhaleemmh@yahoo.com
Received 5 January 2015; accepted 22 January 2015; published 26 January 2015
Copyright © 2015 by authors and OALib.
This work is licensed under the Creative Commons Attribution International License (CC BY).
http://creativecommons.org/licenses/by/4.0/
Abstract
The Hantzsch amide derivatives 1 are prepared by reaction of a mixture of two moles of benzoy-
lacetone, 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. Pyridi-
nethione 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 isothiocya-
nate afforded 10, 11 and 13. Reactions of 3 with arylidenemalononitrile 14 in ethanolic triethyla-
mine yielded 1:1 addact 17a-c.
Keywords
Pyridines, Pyrimidines, Pyridinthione, Pyridothienopyrimidine and Isoquinolines
Subject Areas: Analytical Chemistry, Organic Chemistry
1. Introduction
Polyfunctionally substituted 1,4-dihydropyridines have been widely explored as cardiovascular agents. Nifedi-
pine has been approved for clinical use as an antianginal agent and represents the prototype 1,4-dihydropyridine
(DHP) structure found useful in both antianginal and antihypertensive therapy [1]. Also, the pyridinethione rings
*
Corresponding author.