Synthetic utility of enaminoester moiety in heterocyclic synthesis
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Accepted 2010-07-24
Published 2010-12-22
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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.
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[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
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