European Journal of Chemistry

Facile synthesis of new fused and non-fused heterocyclic systems from a γ-ketoacid

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Published: Mar 31, 2014
DOI: https://doi.org/10.5155/eurjchem.5.1.33-40.900
Keywords:
Thiazole, Quinoxalone, Pyridazinone, Benzocoumarin, Pyrazolothiazole, Thiazolopyridazine
Section
Research Article
Issue
Vol. 5 No. 1 (2014): March 2014
Dates
Received 2013-07-30
Accepted 2013-08-15
Published 2014-03-31


Main Article Content

Marwa Sayed Salem
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
Maher Abd El-Aziz Mahmoud El-Hashash
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
Al-Shimaa Omar Ali Mahmoud
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt
Hassan Mohamed Fawzy Madkour
Synthetic Organic Chemistry Laboratory, Chemistry Department, Faculty of Science, Ain Shams University, Abbasiya, Cairo, 11566, Egypt

Abstract

The chemical reactivity of 4-(2-tetryl)-4-oxobut-2-enoic acid towards carbon, nitrogen, oxygen, sulfur nucleophiles and binucleophiles namely o-phenylenediamine, o-aminophenol, and o-aminothiophenol has been studied. The investigated nucleophilic reactions result in the formation of heterocyclic compounds with fused and non-fused systems namely, pyridazinone, tetrhydroquinoline, quinoxalone, oxazinone, thiazole and benzocoumarin.


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(1)
Salem, M. S.; El-Hashash, M. A. E.-A. M.; Mahmoud, A.-S. O. A.; Madkour, H. M. F. Facile Synthesis of New Fused and Non-Fused Heterocyclic Systems from a γ-Ketoacid. Eur. J. Chem. 2014, 5, 33-40.

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References

[1]. Kirchner, F. K.; Bailey, J. H.; Cavallito, C. J. J. Am. Chem. Soc. 1949, 71, 1210-1213.
http://dx.doi.org/10.1021/ja01172a020

[2]. Dal Pozzo, A.; Acquasaliante, M.; Donezzeli, G.; De Maria, P.; Nicoli, C. J. Med. Chem. 1987, 30(9), 1674-1677.
http://dx.doi.org/10.1021/jm00392a026

[3]. Bowden, K.; Dal Pozzo, A.; Duah, C. K. J. Chem. Res. (S) 1990,12, 2801-2830.

[4]. Teichert, A.; Lubken, T.; Schmidt, J.; Porzel, A.; Arnold, N.; Wessjohann, L. Z. Naturforsch. B 2005, 60, 25-32.

[5]. Cramer, B.J.; Schroeder, W.; Moran, W.J.; Nield, C.H.; Edwards, M.; Jarowski, C.I.; Puetzer, B. J. Am. Pharm. Assoc. Sci. 1948, 37(11), 439-449.
http://dx.doi.org/10.1002/jps.3030371102

[6]. Bianchi, M.; Butti, A.; Christidis, Y.; Perronnet, J.; Barzaghi, F.; Cesana, R.; Nencioni, A. Eur. J. Med. Chem. 1988, 23, 45-52.
http://dx.doi.org/10.1016/0223-5234(88)90166-3

[7]. Todorovic, M. D. V.; Nikolic A. E.; Kolundzija, B.; Hamel, E.; Ristic, S.; Juranic, I. O.; Drakulic, B. J. Eur. J. Med. Chem. 2013, 62, 40-50.
http://dx.doi.org/10.1016/j.ejmech.2013.01.006

[8]. Tsentalovich, Y. P.; Sherin, P. S.; Kopylova, L. V.; Cherepanov, I. V.; Grilj, J.; Vauthey, E. Invest. Ophth. Vis. Sci. 2011, 52(10), 7687-7696.
http://dx.doi.org/10.1167/iovs.11-8120

[9]. Juranic, Z.; Stevovic, L. j.; Drakulic, B.; Stanojkovic, T.; Radulovic, S.; Juranic, I. J. Serb. Chem. Soc. 1999, 64, 505-512.

[10]. Drakulic, B. J.; Stanojkovic, T. P.; Zizak, Z. S.; Dabovic, M. M. Eur. J. Med. Chem. 2011, 46, 3265-3273.
http://dx.doi.org/10.1016/j.ejmech.2011.04.043

[11]. El-Hashash, M. A.; Soliman, M. H. A.; Abd El-Gwad, I. I.; El-Sakka, S. S.; Morsy, M. A. Afinidad 2010, 67(548), 367-373.

[12]. Youssef, A. S. A.; Marzouk, M. I.; Madkour, H. M. F.; El-Soll, A. M. A.; El-Hashash, M. A. Can. J. Chem. 2005, 83, 251-259.
http://dx.doi.org/10.1139/v05-045

[13]. Madkour, H. M. F.; Baloch, N.; Salem, M. S.; Al-kahraman, Y. M. S. A.; Lashlam, M. B. Arch. Sci. 2012, 65(12), 349-356.

[14]. Baloch, N.; Alkahraman,Y. M. S. A.; Zaidi, M. A.; Madkour, H. M. F. GJSFR (B) Global J. Sci. Fro. Res. -B: Chem. 2012, 12(1), 27-32.

[15]. Salem, M. S.; Marzouk, M. I.; Ali, S. N.; Madkour, H. M. F. Eur. J. Chem. 2012, 3(2), 220-227.
http://dx.doi.org/10.5155/eurjchem.3.2.220-227.592

[16]. Madkour, H. M. F. Heterocycles 1993, 36 (5), 947-959.
http://dx.doi.org/10.3987/COM-92-6079

[17]. Al-Kahraman,Y. M. S. A.; Madkour, H. M. F.; Ali; D.; Yasinzai M. Molecules 2010, 15, 660-671.
http://dx.doi.org/10.3390/molecules15020660

[18]. Al-Kahraman, Y. M.S.; Madkour, H. M. F.; Sajid, M.; Azim, M. K.; Bukhari, I.; Yasinzai, M. World J. Chem. 2011, 6(1), 19-24.

[19]. Madkour, H. M. F.; El-Shiekh, Y. W.; Ahmed, A. F. A.; Farag, A. A. Middle- East J. Sci. Res. 2011, 9(4), 520-526.

[20]. Papa, D.; Schwenk, E.; Villani, F.; Klingsberg, E. J. Am. Chem. Soc., 1948, 70 (10), 3356-3360
http://dx.doi.org/10.1021/ja01190a041

[21]. Orlov, V. D.; Kolos, N. N.; Yaremenko, F. G.; Lavrushin, V. F. Khim Geterotsikl. 1980, 5, 697-700 [Chem. Heterocyc. Compd. 16, (1980) (Eng)].

[22]. Orlov, V. D.; Kolos, N. N.; Rozhko, L. I.; Yaremenko, F. G.; Zolotarev, B. M.; Lavrushin, V. F. Khim. Geterotsikl. 1981, 6, 747-755 [Chem. Heterocyc. Compd. 17, 1981 (Engl)].

[23]. Kotake, M.; Sakan, T.; Senoh, S. J. Am. Chem. Soc. 1951, 73, 1832-1834.
http://dx.doi.org/10.1021/ja01148a125

[24]. Tomisawa, K.; Kammeo, K.; Matsunaga, T.; Saito, S.; Hosoda, K.; Asami, Yu.; Sota, K. Chem. Pharm. Bull. 1985, 33(6), 2386-2394
http://dx.doi.org/10.1248/cpb.33.2386

[25]. Kameo, K.; Asami, Yu.; Ogawa, K.; Takeshita, K.; Saito, S.; Tomisawa, K.; Sota, K. Chem. Pharm. Bull. 1988, 36(6), 2050-2060.
http://dx.doi.org/10.1248/cpb.36.2050

[26]. Kameo, K.; Asami, Yu.; Ogawa, K.; Matsunago, K.; Saito, S.; Tomisawa, K.; Sota, K. Chem. Pharm. Bull. 1989, 37(5), 1260-1267.
http://dx.doi.org/10.1248/cpb.37.1260

[27]. Evoy, F. J. Mc.; Lai, F. M.; Albright, J. D. J. Med. Chem. 1983, 26, 381-394.

[28]. Pinto, I. L.; Jarvest, R. L.; Clark, B.; Dabrowski, Ch. E.; Fenwick, A.; Gorczyca, M. M.; Jennings, L. J.; Lavery, P.; Sterberg, E. J.; Tew, D. G.; West, A. Bioorg. Med. Chem. Lett. 1983, 9449-9459.

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