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

Güleser Abacı Sevim Rollas Esra Tatar

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

Keywords

1 , 2 , 4-triazole-5-thione , synthesis , method development

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

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.