1,2,4-Triazine Chemistry Part I: Orientation of cyclization reactions of functionalized 1,2,4-triazine derivatives

Reda Mohammady Abdel-Rahman, Mohammed Saleh Tawfik Makki, Tarik El-Sayed Ali, Magdy Ahmed Ibrahim

Abstract


Orientation of heterocyclization reactions of functionalized 1,2,4-triazines were studied by effect of substituents in 1,2,4-triazine moieties, type of the solvent used in the reaction and the temperature effect. Also, it was found that cyclization process depended mainly on the chemoselective and regioselectivity states of the parent substrate as well as preferring cite of ring closure.

1_3_236_245_800


Keyword(s)


1,2,4-Triazines; Chemical reactivity; Cyclization reactions

European Journal of Chemistry, 1 (3), (2010), 236-245

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DOI: http://dx.doi.org/10.5155/eurjchem.1.3.236-245.54

 

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References

[1]. Ibrahim, M. A.; Abdel-Rahman, R. M.; Abdel-Halim, A. M.; Ibrahim, S. S.; Allimony, H. A. J. Braz. Chem. Soc. 2009, 20, 1275-1286.

[2]. Ali, T. E. Eur. J. Med. Chem. 2009, 44, 4539-4546.
doi:10.1016/j.ejmech.2009.06.022
PMid:19615792

[3]. Ali, T. E. Eur. J. Med. Chem. 2009, 44, 4385-4392.
doi:10.1016/j.ejmech.2009.06.022
PMid:19615792

[4]. Kamble, R. R.; Sudha B. S. J. Chem. Sci. 2006, 118, 191-194.
doi:10.1007/BF02708472

[5]. Ibrahim, M. A.; Abdel-Rahman, R. M.; Abdel-Halim, A. M.; Ibrahim, S. S.; Allimony, H. A. Arkivoc 2008, xvi, 202-215.

[6]. Abdel-Rahman, R. M. Trends Heterocycl. Chem. 1999, 6, 126-133.

[7]. Abdel-Rahman, R. M. Pharmazie 1999, 54, 791-804.
PMid:10603605

[8]. Abdel-Rahman, R. M. Phosphorus Sulfur, Silicon and Relat. Elem. 2000, 166, 315-357.
doi:10.1080/10426500008076552

[9]. Abdel-Rahman, R. M. Pharmazie 2001, 56, 275-286.
PMid:11338663

[10]. Abdel-Rahman, R. M. Pharmazie 2001, 56, 18-30.
PMid:11210661

[11]. Abdel-Rahman, R. M. Pharmazie 2001, 56, 195-212.
PMid:11265582

[12]. Abdel-Rahman, R. M. Trends Heterocycl. Chem. 2002, 8, 187-194.

[13]. Daunis, J.; Follet, M. Bull. Soc. Chim. Fr. 1975, 857-862; Chem. Abstr. 1975, 83, 335.

[14]. Abdel-Rahman, R. M. Indian J. Chem. 1988, 27B, 548-552.

[15]. Joshi, K. C.; Pathak, V. N.; Bhargava, S. J. Inorg. Nuclear Chem. 1977, 39, 803-810.
doi:10.1016/0022-1902(77)80159-0

[16]. Morsy, J. M.; Ismail, F.; Abdel-Rahman, R. M. Pak. J. Sci. Ind. Res. 2000, 43, 214-219.

[17]. Pal, R.; Jain, K.; Gupta, G. D.; Handa, R. N.; Pujari, H. K. Indian J. Chem. 1991, 30B, 1098-1102.

[18]. Mohan, J.; Kumar, A. Indian J. Chem. B, Org. Chem. Including Med. Chem. 2002, 41B, 2364-2370.

[19]. Shafiee, A.; Lalezari, I. J. Heterocycl. Chem. 1971, 8, 1011-1014.
doi:10.1002/jhet.5570080622

[20]. Abdel-Rahman, R. M. Farmaco 1991, 46, 379-384.
PMid:1859590

[21]. Abdel-Rahman, R. M.; Seada, M.; Fawzy, M.; El-Baz, I. Pharmazie 1994, 49, 11-17.

[22]. Ali, M. I.; Abdel-Fattah, A. M.; Hammouda, H. A.; Hussein, S. M. J. Indian Chem. Soc. 1975, 13, 109-115.

[23]. Gieies, A. A.; Abdel-Hafez, A. A.; Kamal El-Dean, A. M.; Hozien, Z. A. Bull. Fac. Sci. 1993, B22, 37-46; Chem. Abstr. 1995, 122, 56020.

[24]. Eid, M. M.; Hassan, R. A. Egypt J. Pharm. Sci. 1991, 31, 337-342.

[25]. Abdel-Rahman, R. M; Fawazy, M. M. Pak. J. Sci Ind. Res. 1992, 32, 69-75.

[26]. El-Gendy, Z.; Morsy, J. M.; Allimony, H. A.; Abdel-Momen, W. R. Abdel-Rahman, R. M. Phosphorus Sulfur, Silicon and Relat. Elem. 2003, 178, 2055-2071.
doi:10.1080/10426500390228738

[27]. Kobets, N. N.; Kruglenko, V. P.; Kablova, M. S.; Timoshin; A. A. UK. Khim. Zh. 1984, 50, 111-119; Chem. Abstr., 1985, 102, 95615r.

[28]. Tadachi, S.; Eikah, I. J. Heterocycl. Chem. 1981, 18, 1353-1356.
doi:10.1002/jhet.5570180716

[29]. Mansour, A. K.; Awad, S. B.; Antoun, S. Z. Naturforsch B 1974, 29, 625-628.

[30]. Ali, M. I.; El-Sayed A. A.; Hammouda, H. A. J. Prakt Chem. 1974, 316, 163-173; Chem. Abstr. 1974, 81, 49660b.

[31]. Abdel-Rahman, R. M. Indian J. Chem. 1986, 25B, 815-821.

[32]. Abdel-Rahman, R. M.; Abdel-Malik, M. S. Pak. J. Sci. Ind. Res. 1990, 33, 142-146.

[33]. Daunis, J.; Follet, M. Bull. Soc. Chim. Fr. 1975, 864-869; Chem. Abstr. 1975, 83, 114345.

[34]. Abdel-Rahman, R. M.; Fawzy, M. M.; El-Gendy, Z. Asian J. Chem. 1992, 4, 534-538.

[35]. Singh, H.; Yadov, L.; Singh, A. K. J. Indian Chem. Soc. 1985, 62, 147-154.

[36]. Gamal, A. J. Indian Chem. Soc. 1997, 74, 624-628.

[37]. Abdel Hamid, H.; Moussad, A.; Ramadan, E.; El-Ashry, E. H. Heterocycl. Commun. 1999, 5, 473-478.

[38]. Abdel-Monem, W. R.; Abdel-Rahman, R. M. Inter. J. Chem. 2006, 16, 1-6.

[39]. Rami, V. J. Liebigs Ann. Chem. 1988, 11, 1089-1094.
doi:10.1002/jlac.198819881113

[40]. Haban, M. A. E; Nasr, A. Z.; Morgaan, A. E. A. Farmaco 1999, 54, 800-809.
doi:10.1016/S0014-827X(99)00107-X

[41]. Trepamier, D.; Krieges, L.; Paul, E. J. Heterocycl. Chem.1971, 8, 621-627.
doi:10.1002/jhet.5570080416

[42]. Abdel-Rahman, R. M., Morsy, J. M.; Hanafy, F.; Amine, H. Pharmazie 1999, 54, 347-355.
PMid:10368828

[43]. Ali, T. E.; Abdel-Rahman, R. M.; Hanafy, F. I.; El-Edfawy, S. M. Phosphorus Sulfur, Silicon and Relat. Elem. 2008, 183, 2565-2577.
doi:10.1080/10426500801967864

[44]. Trepamier, D. L.; Kriger, P. E. J. Heterocycl. Chem. 1970, 7, 1231-1235.
doi:10.1002/jhet.5570070601

[45]. Shawali, A. S.; Gomha, S. M. Tetrahedron 2002, 58, 8559-8564.
doi:10.1016/S0040-4020(02)00946-8

[46]. Mojzych, M.; Karczmarzyk, Z.; Rykowski, A. J. Chem. Cryst. 2005, 35, 151-153.
doi:10.1007/s10870-005-2805-4

[47]. Goodman, M. M.; Paudler, W. W. J. Org. Chem. 1977, 42, 1866-1869.
doi:10.1021/jo00431a009

[48]. Joshi, K. C.; Chand, P. J. Heterocycl. Chem. 1980, 17, 1783-1784.
doi:10.1002/jhet.5570170830

[49]. Hajos, G.; Messmer, A.; Neszmely, A. Parkanyi, L. J. Org. Chem. 1984, 49, 3199-3203.
doi:10.1021/jo00191a029

[50]. Moussad, A.; Abdel Hamid, A. A.; Elnemr, A.; El-Ashry, E. H. Bull. Chem. Soc. Japan 1992, 65, 546-553.
doi:10.1246/bcsj.65.546

[51]. Abdel-Rahman, R. M.; Abdel-Monem, W. R. Indian J. Chem. 2007, 46B, 838-846.

[52]. Volovenko, Y. M.; Resnyanskaya; E. V. Mendeleev Commun. 2002, 12, 119-120.
doi:10.1070/MC2002v012n03ABEH001580

[53]. Ali, A. A.; Hassan, A. A.; Mourad A. E. Can. J. Chem. 1993, 71, 1845-1849.
doi:10.1139/v93-231


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