

Synthetic utility of enaminoester moiety in heterocyclic synthesis
Hassan Mohamed Fawzy Madkour (1)





(1) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya,Cairo, EG-11566, Egypt
(2) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya,Cairo, EG-11566, Egypt
(3) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya,Cairo, EG-11566, Egypt
(4) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya,Cairo, EG-11566, Egypt
(5) Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya,Cairo, EG-11566, Egypt
(*) Corresponding Author
Received: 12 Apr 2010 | Revised: 21 Jul 2010 | Accepted: 24 Jul 2010 | Published: 22 Dec 2010 | Issue Date: December 2010
Abstract
Thieno[2,3-b]pyridine-2-carboxylate was utilized to construct a variety of new heterocyclic systems such as thienopyrimidinone, thienopyridine and pyridothienoxazinone derivatives. Treatment of pyridothienoxazinone derivative with some other nitrogen nucleophiles afforded 3-substituted-pyridothienopyramidinone derivatives. Secondary amines such as morpholine, piperidine and N-methylaniline reacted smoothly with the oxazinone derivative. When the oxazinone derivative was allowed to react with ethanol containing few drops of pyridine or formamide as a basic catalyst and heated to reflux, afforded thienopyridine ester. All the compounds were fully characterized by means of IR, MS, 1H NMR spectra and elemental analyses.
Announcements
One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and May 31, 2023 (Voucher code: SPONSOR2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.1.4.352-359.61
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Citations
[1]. Marwa S. Salem, Sameh I. Sakr, Waled M. El-Senousy, Hassan M. F. Madkour
Synthesis, Antibacterial, and Antiviral Evaluation of New Heterocycles Containing the Pyridine Moiety
Archiv der Pharmazie 346(10), 766, 2013
DOI: 10.1002/ardp.201300183

References
[1]. Madkour, H. M. F.; Afify, A. A. E.; Abdelaal, A. A.; El-Sayed, G. A.; Salem, M. S. Phosphorus, Sulfur, Silicon and the Relat. Elem. 2009, 184(3), 719-732.
doi:10.1080/10426500802266407
[2]. Madkour, H. M. F.; Afify, A. A. E.; El-Sayed, G. A.; Salem, M. S. Bul. Chem. Commun. 2008, 40 (2), 147-159.
[3]. Madkour, H. M. F.; Mahmoud, M. R.; Sakr, A. M.; Habashy, M. M. Sci. Pharm. 2001, 69, 33-52 .
[4]. Salem, M. A. I.; Madkour, H. M. F.; Soliman, E. A.; Mahmoud, N. F. H. Heterocycles. 2000, 53 (5), 1129-1143.
doi:10.3987/COM-98-8232
[5]. Azab, M. E.; Ibraheem, M. A. E.; Madkour, H. M. F. Phosphorus, Sulfur, Silicon and the Relat. Elem. 2006, 181, 1299-1313.
doi:10.1080/10426500500326834
[6]. Bhuiyan, M. H.; Rahman, M.; Hossain, K.; Rahim, A.; Hossain, M. I.; Abu Naser, M. Acta Pharm. 2006, 56, 441-450.
PMid:19839136
[7]. Bedair, A. H.; El-Hady, N. A.; AbdEl-Latif, M. S.; Fakery, A. H.; El-Agrody, A. M. Il Farmaco. 2000, 55, 708-714.
doi:10.1016/S0014-827X(00)00097-5
[8]. Ghorab, M. M.; Abdel-Gawad, S. M.; El-Gaby, M. S. A. Il Farmaco. 2000, 55, 249-255.
doi:10.1016/S0014-827X(00)00029-X
[9]. Irwin, W. J.; Wibberley, D. G. Adv. Heterocycl. Chem. 1969, 10, 149-198.
doi:10.1016/S0065-2725(08)60497-3
[10]. Robins, R. K.; Srinivasta, P. C.; Revankar, G. P.; Novinson, T.; Miller, J. P. Lect. Heterocycl. Chem. 1982, 6, 93-103.
[11]. Büchel, K. H. Chemistry of Pesticides, Willey (Interscience) New York, 1983.
[12]. Ashby, J.; Elliott, B. M. Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W., Pergamon, Oxford, 1984; Vol. 1, pp 111.
doi:10.1016/B978-008096519-2.00005-9
[13]. Broom, A. D.; Shim, J. L.; Anderson, G. L. J. Org. Chem. 1976, 41, 1095-1099.
doi:10.1021/jo00869a003
PMid:1255289
[14]. Landquist, J. K. Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C. W. Pergamon, Oxford, 1984; Vol. 1, pp 144.
[15]. Skipper, H. E.; Robins, R. K.; Thomson, J.R.; Cheng, C. C.; Brockman, R. W.; Schmahl, F. M. Jr. Cancer Res. 1957, 17, 579-596.
PMid:13446843
[16]. Artemov, V. A., Ph. D. (Chem.) Thesis; Zelinsky, N. D. Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, 1995; pp183.
[17]. Litvinov, V. P. Izv. Akad. Nauk, Ser. Khim. 2004, 53(3), 487-516.
[18]. Litvinov, V. P.; Promonenkov, V. K.; Sharanin, Yu. A. and Shestopalov, A. M. Itogi nauki i tekhniki. Ser. Org. Khimii, Advances in Science and Technology. Ser. Organic Chemistry, YINITI, Moscow, 1989; Vol. 17, pp 72.
[19]. Litvinov, V. P.; Rodinovskaya, L. A.; Sharanin, Yu. A.; Shestopalov, A. M.; Senning A. Sulfur Rep. 1992, 13, 1-155.
doi:10.1080/01961779208048951
[20]. Abdel-Hady, S. A.; Badawy, M. A.; Ibrahim, Y. A. Sulfur Lett. 1990, 11(3), 129-137.
[21]. Sasaki, S.; Cho, N.; Nara, Y.; Harada, M.; Endo, S.; Suzuki, N.; Furuya, S.; Fujino, M. J. Med. Chem. 2003, 46 (1), 113-124.
doi:10.1021/jm020180i
PMid:12502365
[22]. Wang, Z.; Neidlein, R.; Krieger, C. Synthesis. 2000, 255-258 .
doi:10.1055/s-2000-6249
[23]. Youssef, K. M. Al-Azhar Bull. Sci. 1999, 10(1), 89-97.
[24]. Nassan, O. M.; Hassan, A. Y.; Heiba, H. I.; Ghorb, M. M. Al-Azhar Bull. Sci. 1997, 8(2), 435-444.
[25]. Heiba, H. I.; Ghorab, M. M.; Amin, N. E.; Ramadan, L. Egypt. J. Biotechnol. 1998, 4, 16-30.
[26]. Arita, M.; Hukumasu, Y.; Sano, M.; Hoshino, Y.; Komatsu, H., PCT Int., 08, 113, 1989: Chem. Abstr. 1990, 112, 98533.
[27]. Chaykovsky, M.; Lin, M.; Rosowsky, A.; Modest, E. J. J. Med. Chem. 1973, 16, 188-191.
doi:10.1021/jm00261a003
PMid:4632694
[28]. Hozien, Z. A.; Abdel-Wahab, A. A.; Hassan, K. M.; Atta, F. M.; Ahmed, S. A. Pharmazie 1997, 52, 753-758.
PMid:9362089
[29]. Rosowsky, A.; Chaykovsky, M.; Chen, K. K. N.; Lin, M.; Modest, E. J. J. Med. Chem. 1973, 16(3), 185-187.
doi:10.1021/jm00261a002
PMid:4632693
[30]. Rosowsky, A.; Chen, K. K. N.; Lin, M. J. Med. Chem. 1973, 16(3), 191-194.
doi:10.1021/jm00261a004
PMid:4632695
[31]. Kapustina, M. V.; Omel’kin, O. Yu.; Kharizomenova, I. A.; Shvedov, V. I.; Felitis, L. N. Khim.-farm. Zh. 1991, 25(7), 38-39.
[32]. Furuya, S.; Suzuki, N. PCT Int. 78, 780, 2001: Chem. Abstr. 2001, 135, 313627w.
[33]. Rottlaender, M.; Graven, S. A.; Feldin, J.; Pederen, J.T.; Andersen.; K.; Moltzen, E. K.; Langgard, K. J.; Balle, T. PCT Int. 64, 428, 2003: Chem. Abstr. 2003, 139, 164807h.
[34]. Daiichi Seiyaku Co. Ltd. Jpn. Kokai, 77, 687, 1982: Chem. Abstr. 1982, 97, 163007.
[35]. Wang, L.; Reng, J. B.; Liu, J. Li.; Yuan, J. Zhongguo Yoake Daxue Xuebao. 1998, 29, 331-333.
[36]. Calhelha, R. C.; Queiroz, M. -J. R. P. Tetrahedron Lett. 2010, 51, 281-283.
doi:10.1016/j.tetlet.2009.10.138
[37]. Thompson, W. J.; Gaudino, J. J. Org. Chem. 1984, 49 (26), 5237-5243.
doi:10.1021/jo00200a045
[38]. Detsi, A.; Bardakos, V.; Markopoulo, J.; Markopoulo, A. I. J. Chem. Soc. Perkin Trans I 1996, 2909-2913.
[39]. Cohn, O. M.; Narine, B. J. Chem. Reasearch (S) 1977, 294: Chem. Abstr. 1978, 88, 105040h
[40]. Desideri, N.; Manna, F.; Stein, M. L. J. Heterocycl. Chem. 1981, 18(6), 1085-1087.
doi:10.1002/jhet.5570180605
[41]. Shiba, S. H.; El-Khamry, A. A.; Shaban, M. E.; Atia, A. S. Pharmazie. 1997, 52(3), 189-194.
PMid:9109167
[42]. Alyaa, A. S.; Abdel Momen, A. E.; Sayed, A. S.; Abdelaal, A. A. Archiv. Der pharmazie. 2000, 333, 365-372.
doi:10.1002/1521-4184(200011)333:11<365::AID-ARDP365>3.0.CO;2-2
[43]. Çelik, I.; Kanışkan, N.; Kökten, S. Tetrahedron 2009, 65 (1), 328-335.
doi:10.1016/j.tet.2008.10.047
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.1.4.352-359.61

















European Journal of Chemistry 2010, 1(4), 352-359 | doi: https://doi.org/10.5155/eurjchem.1.4.352-359.61 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.