Synthesis of 1,2,4-Triazoles via Oxidative Heterocyclization: Selective C-N Bond Over C-S Bond Formation

The Journal of Organic Chemistry
Anupal GogoiBhisma K Patel

Abstract

The higher propensity of C-N over C-S bond forming ability was demonstrated, through formal C-H functionalization during the construction of 4,5-disubstituted 1,2,4-triazole-3-thiones from arylidenearylthiosemicarbazides catalyzed by Cu(II). However, steric factors imparted by the o-disubstituted substrates tend to change the reaction path giving thiodiazole as the major or an exclusive product. Upon prolonging the reaction time, the in situ generated thiones are transformed to 4,5-disubstituted 1,2,4-triazoles via a desulfurization process. Two classes of heterocycles viz. 4,5-disubstituted 1,2,4-triazole-3-thiones and 4,5-disubstituted 1,2,4-triazoles can be synthesized from arylidenearylthiosemicarbazides by simply adjusting the reaction time. Desulfurization of 1,2,4-triazole-3-thiones is assisted by thiophilic Cu to provide 1,2,4-triazoles with concomitant formation of CuS and polynuclear sulfur anions as confirmed from scanning electron microscope and energy dispersive X-ray spectroscopy measurements. A one-pot synthesis of an antimicrobial compound has been successfully achieved following this strategy.

References

Jun 1, 1988·Journal of Medicinal Chemistry·J M KaneF P Miller
May 1, 1966·Journal of Medicinal Chemistry·H A Burch, W O Smith
Jul 19, 1996·Journal of Medicinal Chemistry·Y NaitoY Kagitani
Jun 27, 2001·Bioorganic & Medicinal Chemistry Letters·I KüçükgüzelM Kiraz
Dec 19, 1996·Chemical Reviews·George A. Patani, Edmond J. LaVoie
Feb 20, 2002·Chemical Reviews·Alexander E. Shilov, Georgiy B. Shul'pin
May 11, 2002·The Journal of Organic Chemistry·Yukio HitotsuyanagiKoichi Takeya
Aug 31, 2002·Angewandte Chemie·Martin E BluhmManfred Döring
Oct 17, 2003·European Journal of Medicinal Chemistry·Alireza ForoumadiAfsaneh Rahmani
Mar 12, 2005·Angewandte Chemie·Neil BurfordAndreas Decken
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
Jul 20, 2007·Journal of Medicinal Chemistry·Joseph P MarinoScott K Thompson
Nov 2, 2007·Chemical Reviews·Egle M BeccalliSilvia Sottocornola
Aug 14, 2008·Chemical Reviews·M Mar Díaz-Requejo, Pedro J Pérez
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
May 15, 2009·Chemistry : a European Journal·Praew Thansandote, Mark Lautens
Jun 26, 2009·Accounts of Chemical Research·Olafs DaugulisDmitry Shabashov
Mar 1, 2007·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Mohammad Amir, Shikha Kumar
Jan 14, 2010·Chemical Reviews·David BalcellsOdile Eisenstein
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Jan 21, 2010·Chemical Communications : Chem Comm·Chang-Liang SunZhang-Jie Shi
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
Mar 4, 2010·Journal of the American Chemical Society·Bo QianHanmin Huang
May 8, 2010·Chemical Communications : Chem Comm·Tatsuya FukutaniMasahiro Miura
Sep 11, 2010·European Journal of Medicinal Chemistry·Imtiaz KhanM Iqbal Choudhary
Jan 6, 2011·Journal of the American Chemical Society·Andy S TsaiJonathan A Ellman
Feb 10, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Arghya Basu, Gopal Das

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Citations

Mar 14, 2019·Mini Reviews in Medicinal Chemistry·Ankit Jain, Poonam Piplani
Oct 24, 2020·Current Topics in Medicinal Chemistry·Ana I MatesanzAdoración G Quiroga

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