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Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives

Year 2013, Volume: 17 Issue: 3, 181 - 186, 07.03.2014

Abstract

ABSTRACT: 3,4-Disubstituted-2,4-dihydro-5H-1,2,4-triazole-5-thiones were synthesized by a
new one-pot, two-step synthesis method which was demonstrated to be superior than the
current synthesis methods. The new method involves addition of alkyl/aryl isothiocyanates
to substituted hydrazides in ethanol following the refluxing process of intermeadiate in 4N
sodium hydroxide solution. According to our new synthesis procedure, reaction has gone to
completion within 6 hours by higher product yields and reduced solvent usage.
KEYWORDS: 1,2,4-triazole-5-thione, synthesis, method development

References

  • Barbuceanu SF, Saramet G, Almajan GL, Draghici C, Barbuceanu F, Bancescu G. New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation. Eur J Med Chem 2012; 49: 417-23.
  • Padmaja A, Muralikrishna A, Rajasekhar C, Padmavathi V. Synthesis and antimicrobial activity of pyrrolyl/ pyrazolyl arylaminosulfonylmethyl 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Chem Pharm Bull (Tokyo) 2011; 59: 1509-17.
  • Eswaran S, Adhikari AV, Shetty NS. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur J Med Chem 2009; 44: 4637-47.
  • Gülerman NN, Dogan HN, Rollas S, Johansson C, Celik C. Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. Farmaco 2001; 56: 953-8.
  • Rollas S, Kalyoncuoğlu N, Sür-Altiner D, Yeğenoğlu Y. 5-(4-Aminophenyl)-4-substituted-2,4-dihydro-3H1,2,4-triazole-3-thiones: synthesis and antibacterial and antifungal activities. Pharmazie 1993; 48: 308-9.
  • Sharma V, Bhatia R. Triazoles in antifungal theraphy: a review. Int J Res Pharm Biomed 2011; 2: 417-27.
  • Kandemirli F, Shvets N, Ünsalan S, Küçükgüzel İ, Rollas S, Kovalishyn V, Dimoglo A. The structure-antituberculosis activity relationships study in a series of 5-(4-aminophenyl)-4-substituted-2,4-dihydro-3H-1,2,4triazole-3-thione derivatives. A combined electronictopological and neural networks approach. Med Chem 2006; 2: 415-22.
  • Küçükgüzel İ, Küçükgüzel ŞG, Rollas S, Kiraz M. Some 3-thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials. Bioorg Med Chem Lett 2001; 11: 1703-7.

Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives

Year 2013, Volume: 17 Issue: 3, 181 - 186, 07.03.2014

Abstract

References

  • Barbuceanu SF, Saramet G, Almajan GL, Draghici C, Barbuceanu F, Bancescu G. New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation. Eur J Med Chem 2012; 49: 417-23.
  • Padmaja A, Muralikrishna A, Rajasekhar C, Padmavathi V. Synthesis and antimicrobial activity of pyrrolyl/ pyrazolyl arylaminosulfonylmethyl 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Chem Pharm Bull (Tokyo) 2011; 59: 1509-17.
  • Eswaran S, Adhikari AV, Shetty NS. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur J Med Chem 2009; 44: 4637-47.
  • Gülerman NN, Dogan HN, Rollas S, Johansson C, Celik C. Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities. Farmaco 2001; 56: 953-8.
  • Rollas S, Kalyoncuoğlu N, Sür-Altiner D, Yeğenoğlu Y. 5-(4-Aminophenyl)-4-substituted-2,4-dihydro-3H1,2,4-triazole-3-thiones: synthesis and antibacterial and antifungal activities. Pharmazie 1993; 48: 308-9.
  • Sharma V, Bhatia R. Triazoles in antifungal theraphy: a review. Int J Res Pharm Biomed 2011; 2: 417-27.
  • Kandemirli F, Shvets N, Ünsalan S, Küçükgüzel İ, Rollas S, Kovalishyn V, Dimoglo A. The structure-antituberculosis activity relationships study in a series of 5-(4-aminophenyl)-4-substituted-2,4-dihydro-3H-1,2,4triazole-3-thione derivatives. A combined electronictopological and neural networks approach. Med Chem 2006; 2: 415-22.
  • Küçükgüzel İ, Küçükgüzel ŞG, Rollas S, Kiraz M. Some 3-thioxo/alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials. Bioorg Med Chem Lett 2001; 11: 1703-7.
There are 8 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Güleser Abacı This is me

Sevim Rollas This is me

Esra Tatar

Publication Date March 7, 2014
Published in Issue Year 2013 Volume: 17 Issue: 3

Cite

APA Abacı, G., Rollas, S., & Tatar, E. (2014). Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives. Marmara Pharmaceutical Journal, 17(3), 181-186. https://doi.org/10.12991/mpj.78866
AMA Abacı G, Rollas S, Tatar E. Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives. J Res Pharm. March 2014;17(3):181-186. doi:10.12991/mpj.78866
Chicago Abacı, Güleser, Sevim Rollas, and Esra Tatar. “Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives”. Marmara Pharmaceutical Journal 17, no. 3 (March 2014): 181-86. https://doi.org/10.12991/mpj.78866.
EndNote Abacı G, Rollas S, Tatar E (March 1, 2014) Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives. Marmara Pharmaceutical Journal 17 3 181–186.
IEEE G. Abacı, S. Rollas, and E. Tatar, “Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives”, J Res Pharm, vol. 17, no. 3, pp. 181–186, 2014, doi: 10.12991/mpj.78866.
ISNAD Abacı, Güleser et al. “Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives”. Marmara Pharmaceutical Journal 17/3 (March 2014), 181-186. https://doi.org/10.12991/mpj.78866.
JAMA Abacı G, Rollas S, Tatar E. Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives. J Res Pharm. 2014;17:181–186.
MLA Abacı, Güleser et al. “Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives”. Marmara Pharmaceutical Journal, vol. 17, no. 3, 2014, pp. 181-6, doi:10.12991/mpj.78866.
Vancouver Abacı G, Rollas S, Tatar E. Development of a New and Efficient Synthesis Method of 1,2,4-Triazole-5- Thione Derivatives. J Res Pharm. 2014;17(3):181-6.

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