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SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES

Year 2015, , 44 - 50, 10.07.2015

Ahmet Çetin

https://doi.org/10.12739/NWSA.2015.10.3.3A0072

Abstract

In this study, salicylic and izonicotinic acid hydrazide was converted into 4-amino 5-substituted-4H-1,2,4-triazole-3-thiol 1a,b. A series of [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole-6(5H)-thione 2a,b were prepared from aminomercaptotriazoles. The reaction of aminomercaptotriazole compounds 2a,b with aromatic carboxylic acid and phosphorus oxychloride afforded the newly synthesized 3-substituted-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole derivatives 3a-h in good yields. In addition, the structures of synthesized compounds were confirmed by IR, 1H-NMR and 13C-NMR spectra.

Keywords

1 2 4-triazole Aminomercaptotriazoles Thiadiazole Hydrazide Phosphorus Oxychloride.

References

  • Cansiz, A., Orek, C., Koparir, M., Koparir, P., and Cetin, A., (2012). 4-Allyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione: Synthesis, Experimental and Theoretical Characterization, Spectrochimica Acta Part A-Molecular and Bimolecular Spectroscopy, 91, 136-145.
  • Holla, B.S., Poojary, K.N., Rao, B.S., and Shivananda, M.K., (2002). New Bis-aminomercaptotriazoles and Bistriazolo Thiadiazoles as Possible Anticancer Agents, Eur. J. Med. Chem.,37, 511-517.
  • Holla, B.S. and Kalluraya, B., (1988). Synthesis of some substituted 4-(5-nitro-2-furfurylidenamino)-5-mercapto-1,2,4-triazoles and 7H-6-(5-nitro-2-furyl)-s-triazolo[3,4-b] [1,3,4] thiadiazines, Indian Journal of Chemistry, 27B, 683-685.
  • Zhang, Z.Y. and Xiao-Wen, S., (1998). Heterocycles, 48, 561-584.
  • Pandeya, S.N., Sriram, S., Nath, G., and DeClercq, E., (2000). Syntehesis, Antibacterial, Antifungal and Anti-HIV Evaluation of Schiff and Mannich Bases of Isatin and Its Derivatives with Triazole, Arzneim.-Forsch./Drug Res., 50,55-59.
  • Cansiz, A., Cetin, A., Orek, C., Karatepe, M., Sarac, K., Kus, A., and Koparir, M ., (2012). 6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, Experimental, Theoretical Characterization and Biological Activities, Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 97, 606-615.
  • Menegola, E., Broccia, M. L., Di Renzo, F., and Giavini, E., (2001). Reproductive Toxicology, 15, 421.
  • Abbas, A.A. and Khalil, N.S.A.M., (2005). Nucleosides, Nucleotides, and Nucleic Acids, 24, 1353.
  • Holla, B. S., Sarojini, B. K., Gonsalves, R., (1998), II Farmaco, 53, 395.
  • Ram, V.J., Mishra, L., Pandey, N.H., Kushwaha, D.S., Pieters, L. A.C., and Vlietinck, A.J., (1990). J. Heterocycl. Chem., 27, 351.
  • Koparır, M., Çetin, A., and Cansız, A., (2005). Molecules, 10, 475.
  • Yale, H.L. and Piala, J.J.J., (1966). Med. Chem., 9, 42.
  • Coyanis, E.M., Vedova, D.C.O., Has, A., and Winter, M., (2002). J. of Fluorine Chem., 117, 185.
  • Cansiz, A., Çetin, A., Kutulay, P., and Koparır, M., (2009). Asian Journal of Chem., 21, 617.
  • Dege, N., Andaç, O., Çetin, A., Cansiz, A., Sekerci, M., and Dincer, M., (2005). 5-(Furan-2-yl)-4-(p-tolyl)-2,4-dihydro-1,2,4-triazole-3-thione, Acta Cryst. E61, O17.
  • Dege, N., Ozdemir, N., Cansiz, A., Çetin, A., Sekerci, M., and Dincer, M., (2004). 4-Ethyl-5-(2-hydroxyphenyl)-2H-1,2,4-triazole-3(4H)-thione, Acta Cryst., E60, O1405.
  • Brucato, A., Coppola, A., Gianguzza, S., and Provenzano, P.M., (1978). Bull. Soc. Ital. Biol. Sper., 54, 1051.
  • Coffen, D.L. and Fryer, R.I., (1975). US Patent 3(849): 434, Chemical Abstracts, 82, 730044v.
  • Shiroki, M., Tahara T., and Araki, K., (1975). Japanese Patent No. 75100096, Chemical Abstracts, 84, 59588k.
  • Povelitsa, F.D. and Gural, A.G., (1973). “Antibiotiki” Moscow, Chemical Abstracts, 78, 93044.

BAZI YENİ [1,2,4]TRIAZOLO[3,4-b][1,3,4]TİYADİAZOL TÜREVLERİNİN SENTEZİ VE DENEYSEL KARAKTERİZASYONU

Year 2015, , 44 - 50, 10.07.2015

Ahmet Çetin

https://doi.org/10.12739/NWSA.2015.10.3.3A0072

Abstract

Bu çalışmada, salisilik ve izonikotinik asit hidrazit bileşikleri dönüştürüldü. [1,2,4] triazolo[3,4-b] [1,3,4]tiyadiazol-6(5H)-tiyon 2a,b bileşik serisi aminomerkaptotriazollerden 1a,b sentezlendi. Aminomerkaptotriazol bileşikleri 2a,b ile aromatic karboksilik asit ve fosfor oksiklorürün reaksiyonundan iyi verimle yeni 3-substitüe[1,2,4]triazolo[3,4-b] [1,3,4]tiyadiazol türevleri 3a-h sentezlendi. Sentezlenen bileşiklerin yapıları IR, 1H-NMR and 13C-NMR spektrofotometreleri kullanılarak aydınlatıldı

Keywords

1 2 4-triazol Aminomerkaptotriazoller Tiyadiazol Hidrazit Fosfor Oksiklorür

References

  • Cansiz, A., Orek, C., Koparir, M., Koparir, P., and Cetin, A., (2012). 4-Allyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione: Synthesis, Experimental and Theoretical Characterization, Spectrochimica Acta Part A-Molecular and Bimolecular Spectroscopy, 91, 136-145.
  • Holla, B.S., Poojary, K.N., Rao, B.S., and Shivananda, M.K., (2002). New Bis-aminomercaptotriazoles and Bistriazolo Thiadiazoles as Possible Anticancer Agents, Eur. J. Med. Chem.,37, 511-517.
  • Holla, B.S. and Kalluraya, B., (1988). Synthesis of some substituted 4-(5-nitro-2-furfurylidenamino)-5-mercapto-1,2,4-triazoles and 7H-6-(5-nitro-2-furyl)-s-triazolo[3,4-b] [1,3,4] thiadiazines, Indian Journal of Chemistry, 27B, 683-685.
  • Zhang, Z.Y. and Xiao-Wen, S., (1998). Heterocycles, 48, 561-584.
  • Pandeya, S.N., Sriram, S., Nath, G., and DeClercq, E., (2000). Syntehesis, Antibacterial, Antifungal and Anti-HIV Evaluation of Schiff and Mannich Bases of Isatin and Its Derivatives with Triazole, Arzneim.-Forsch./Drug Res., 50,55-59.
  • Cansiz, A., Cetin, A., Orek, C., Karatepe, M., Sarac, K., Kus, A., and Koparir, M ., (2012). 6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: Synthesis, Experimental, Theoretical Characterization and Biological Activities, Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 97, 606-615.
  • Menegola, E., Broccia, M. L., Di Renzo, F., and Giavini, E., (2001). Reproductive Toxicology, 15, 421.
  • Abbas, A.A. and Khalil, N.S.A.M., (2005). Nucleosides, Nucleotides, and Nucleic Acids, 24, 1353.
  • Holla, B. S., Sarojini, B. K., Gonsalves, R., (1998), II Farmaco, 53, 395.
  • Ram, V.J., Mishra, L., Pandey, N.H., Kushwaha, D.S., Pieters, L. A.C., and Vlietinck, A.J., (1990). J. Heterocycl. Chem., 27, 351.
  • Koparır, M., Çetin, A., and Cansız, A., (2005). Molecules, 10, 475.
  • Yale, H.L. and Piala, J.J.J., (1966). Med. Chem., 9, 42.
  • Coyanis, E.M., Vedova, D.C.O., Has, A., and Winter, M., (2002). J. of Fluorine Chem., 117, 185.
  • Cansiz, A., Çetin, A., Kutulay, P., and Koparır, M., (2009). Asian Journal of Chem., 21, 617.
  • Dege, N., Andaç, O., Çetin, A., Cansiz, A., Sekerci, M., and Dincer, M., (2005). 5-(Furan-2-yl)-4-(p-tolyl)-2,4-dihydro-1,2,4-triazole-3-thione, Acta Cryst. E61, O17.
  • Dege, N., Ozdemir, N., Cansiz, A., Çetin, A., Sekerci, M., and Dincer, M., (2004). 4-Ethyl-5-(2-hydroxyphenyl)-2H-1,2,4-triazole-3(4H)-thione, Acta Cryst., E60, O1405.
  • Brucato, A., Coppola, A., Gianguzza, S., and Provenzano, P.M., (1978). Bull. Soc. Ital. Biol. Sper., 54, 1051.
  • Coffen, D.L. and Fryer, R.I., (1975). US Patent 3(849): 434, Chemical Abstracts, 82, 730044v.
  • Shiroki, M., Tahara T., and Araki, K., (1975). Japanese Patent No. 75100096, Chemical Abstracts, 84, 59588k.
  • Povelitsa, F.D. and Gural, A.G., (1973). “Antibiotiki” Moscow, Chemical Abstracts, 78, 93044.
There are 20 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Chemistry
Authors

Ahmet Çetin

Publication Date July 10, 2015
Published in Issue Year 2015

Cite

APA Çetin, A. (2015). SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES. Physical Sciences, 10(3), 44-50. https://doi.org/10.12739/NWSA.2015.10.3.3A0072
AMA Çetin A. SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES. Physical Sciences. July 2015;10(3):44-50. doi:10.12739/NWSA.2015.10.3.3A0072
Chicago Çetin, Ahmet. “SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES”. Physical Sciences 10, no. 3 (July 2015): 44-50. https://doi.org/10.12739/NWSA.2015.10.3.3A0072.
EndNote Çetin A (July 1, 2015) SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES. Physical Sciences 10 3 44–50.
IEEE A. Çetin, “SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES”, Physical Sciences, vol. 10, no. 3, pp. 44–50, 2015, doi: 10.12739/NWSA.2015.10.3.3A0072.
ISNAD Çetin, Ahmet. “SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES”. Physical Sciences 10/3 (July 2015), 44-50. https://doi.org/10.12739/NWSA.2015.10.3.3A0072.
JAMA Çetin A. SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES. Physical Sciences. 2015;10:44–50.
MLA Çetin, Ahmet. “SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES”. Physical Sciences, vol. 10, no. 3, 2015, pp. 44-50, doi:10.12739/NWSA.2015.10.3.3A0072.
Vancouver Çetin A. SYNTHESIS AND EXPERIMENTAL CHARACTERIZATION OF SOME NEW [1,2,4]TRIAZOLO[3,4-b][1,3,4]THIADIAZOLE DERIVATIVES. Physical Sciences. 2015;10(3):44-50.