Preparation, Characterization, and Potentiometric Titrations of Some New Di-[3-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl] isophthalate/terephthalate Derivatives
3-Alkyl(Aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) reacted with di-(3-formylphenyl) isophthalate (3) and di-(3-formylphenyl) terephthalate (6) to afford the corresponding 6 novel di-[3-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)- azomethinphenyl] isophthalates (4) and 6 novel di-[3-(3-alkyl/aryl-4,5- dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl] terephthalates (7), respectively. The acetylation reactions of compounds 4 and 7 were investigated, and 5 and 8 type compounds were obtained, respectively. The new compounds synthesized were characterized by using IR, 1H-NMR, 13C-NMR, and UV spectral data together with elemental analysis. In addition, to investigate the effects of solvents and molecular structure upon acidity, compounds 4 and 7 were titrated potentiometrically with tetrabutylammonium hydroxide in 5 non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, N,N-dimethylformamide, acetone, and dimethyl sulfoxide). The half-neutralization potential values and the corresponding pKa values were determined for all cases.
Preparation, Characterization, and Potentiometric Titrations of Some New Di-[3-(3-alkyl/aryl-4,5- dihydro-1H -1,2,4-triazol-5-one-4-yl)-azomethinphenyl] isophthalate/terephthalate Derivatives
3-Alkyl(Aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) reacted with di-(3-formylphenyl) isophthalate (3) and di-(3-formylphenyl) terephthalate (6) to afford the corresponding 6 novel di-[3-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)- azomethinphenyl] isophthalates (4) and 6 novel di-[3-(3-alkyl/aryl-4,5- dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinphenyl] terephthalates (7), respectively. The acetylation reactions of compounds 4 and 7 were investigated, and 5 and 8 type compounds were obtained, respectively. The new compounds synthesized were characterized by using IR, 1H-NMR, 13C-NMR, and UV spectral data together with elemental analysis. In addition, to investigate the effects of solvents and molecular structure upon acidity, compounds 4 and 7 were titrated potentiometrically with tetrabutylammonium hydroxide in 5 non-aqueous solvents (isopropyl alcohol, tert-butyl alcohol, N,N-dimethylformamide, acetone, and dimethyl sulfoxide). The half-neutralization potential values and the corresponding pKa values were determined for all cases.
___
- Bhat, A. R.; Bhat, G. V.; Shenoy, G. G. J. Pharm. Pharmacol. 2001, 53, 267-272.
- Modzelewska-Banachiewicz, B.; Jagiello-Wojtowicz, E.; Tokarzewska-Wielosz, E. Acta Pol. Pharm.-Drug Res. , 57, 199-204. Varvaresou, A.; Tsantili-Kakoulidou, A.; Siatra-Papastaikoudi, T.; Tiligada, E. Arzneim.-Forsch./Drug Res. , 50, 48-54. Amir, M.; Khan, M. S. Y.; Zanan, M. S. Indian J. Chem., 2004, 43B, 2189-2194.
- Burzozowski, Z. Acta Pol. Pharm.-Drug Res. 1998, 55, 473-480.
- Katica, C.-R.; Vesna, D.; Vlado, K.; Dora, G. M.; Aleksandra, B. Molecules 2001, 6, 815-824.
- Wang, Z.; You, T.; Xu, Y. Molecules 1996, 1, 68-71.
- Turan-Zitouni, G.; Kaplancıklı, Z. A.; Yıldız, M. T.; Chevallet, P.; Kaya, D. Eur. J. Med. Chem. 2005, 40, 613.
- Karegoudar, P.; Prasad, D. J.; Ashok, M.; Mahalinga, M; Poojary, B.; Holla, B. S. Eur. J. Med. Chem. 2008, , 808-815.
- Y¨uksek, H.; Kolaylı, S.; K¨u¸c¨uk, M.; Y¨uksek, M. O.; Ocak, U.; S¸ahinba¸s, E.; Sivrikaya, E.; Ocak, M. Indian J. Chem. 2006, 45B, 715-718.
- Y¨uksek, H.; Demirba¸s, A.; Ikizler, A.; Johansson, C. B.; C¸ elik, C.; Ikizler, A. A. Arzneim.-Forsch./Drug Res. , 47, 405-409. Alkan, M.; Y¨uksek, H.; G¨ursoy-Kol, ¨O.; Calapo˘glu, M. Molecules 2008, 13 , 107-121.
- Y¨uksek, H.; G¨ursoy, ¨O.; Cakmak, ˙I.; Alkan, M. Magn. Reson. Chem. 2005, 43, 585-587.
- Ikizler, A. A.; Y¨uksek, H. Collect. Czech. Chem. Commun. 1994, 59, 731-735.
- Bah¸ceci, S¸.; Y¨uksek, H.; Ocak, Z.; Azaklı, A.; Alkan, M.; Ozdemir, M. Collect. Czech. Chem. Commun. 2002, , 1215-1222.
- Bah¸ceci, S¸.; Y¨uksek, H.; Ocak, Z.; K¨oksal, C.; Ozdemir, M. Acta Chim. Slov. 2002, 49, 783-794.
- Ikizler, A. A.; Y¨uksek, H. Org. Prep. Proced. Int. 1993, 25, 99-105.
- Y¨uksek, H.; Ocak, Z.; ¨Ozdemir, M.; Ocak, M.; Bekar, M.; Aksoy, M. Ind. J. Heterocycl. Chem. 2003, 13, 49-52.
- Y¨uksek, H.; Ocak, Z.; Alkan, M.; Bah¸ceci, S¸.; ¨Ozdemir, M. Molecules 2004, 9, 232-240.
- Ikizler, A. A.; Ikizler, A.; S¸ent¨urk, H. B.; Serdar, M. Do˘ga-Tr. Kimya D. 1988, 12, 57-66; [Chem. Abstr. 1988, , 238277q].
- Y¨uksek, H.; ¨U¸c¨unc¨u, O.; Alkan, M.; Ocak, Z.; Bah¸ceci, S¸.; ¨Ozdemir, M. Molecules 2005, 10, 961-970.
- Ikizler, A. A.; Erdo˘gan, Y. Do˘ga-Tr. J. Chem. 1991, 15, 337-344; [Chem. Abstr. 1992, 116, 193614y].
- G¨und¨uz, T. Susuz Ortam Reaksiyonları, Gazi B¨uro Kitabevi Tic. Ltd. S¸ti: Ankara, Turkey, 1998.
- Ikizler, A. A.; Un, R. Chim. Acta Turc. 1979, 7, 269-290; [Chem. Abstr. 1991, 94, 15645d].
- Ikizler, A. A.; Ikizler, A.; Y¨uksek, H. Magn. Reson. Chem. 1993, 31, 1088-1094.