Regioselective formation of 1,2,4-triazoles by the reaction of amidrazones in the presence of diethyl azodicarboxylate and catalyzed by triethylamine

Aly, Ashraf A.; Hassan, Alaa A.; Mohamed, Nasr K.; Ramadan, Mohamed; Brown, Alan B.; El-Aal, Amal S. Abd; Bräse, Stefan; Nieger, Martin

doi:10.1007/s11030-018-9868-6

Cited by 5 publications

(2 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Various reports illustrated on the synthesis of triazole-3-thiols from the internal cyclization of acyl hydrazinecarbothioamides in presence of a base [25][26][27]. Aly et al [28] reported on a general method for the synthesis of 1,3,5-trisubstituted 1,2,4triazoles from the reaction of equal equivalents of amidrazones with ethyl azodicarboxylate and Et3N (Mitsunobu reagent) [28]. Under acidic condition, Nacylthiosemicarbazides underwent internal cyclization into 2-amino-1,3,4thiadiazole [29].…”

Section: Figure 1 Representative Examples Of Some 124-triazole-quinol...mentioning

confidence: 99%

Regioselective formation of new 3- S -alkylated-1,2,4-triazole-quinolones

Aly

Elaziz

Elshaier

et al. 2021

Journal of Sulfur Chemistry

Self Cite

View full text Add to dashboard Cite

Regioselective synthesis of quinolone-1,2,4-triazoles was established starting from 4-hydroxyquinol-2-ones. The strategy started by the reaction of ethyl bromoacetate with 4-hydroxyquinoline to give the corresponding ethyl oxoquinolinyl acetates, which reacted with hydrazine hydrate to afford the hydrazide derivatives. Subsequently, hydrazides reacted with isothiocyanate derivatives to give the corresponding acyl thiosemicarbazides. Finally, subjecting the thiosemicarbazide derivatives with ethyl bromoacetate, reaction underwent internal cyclization and alkylation processes. Alkylation occurred regioselectivity to sulfur atom of thione group and not to amino group. Thus 3-S-1,2,4-triazole-quinolones were obtained in good yields. The structure of the obtained compounds was proved by different spectroscopic together with elemental analysis and Xray crystallography.

show abstract

Section: Figure 1 Representative Examples Of Some 124-triazole-quinol...mentioning

confidence: 99%

Regioselective formation of new 3- S -alkylated-1,2,4-triazole-quinolones

Aly

Elaziz

Elshaier

et al. 2021

Journal of Sulfur Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…Figure 5. C-glucopyranosyl 1,2,4-triazoles 56.In 2018, Aly et al[89] reported a general method for the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles 59, 60 from reaction of amidrazones 57 with diethyl azodicarboxylate 58. The authors performed the coupling/cyclisation reaction between N-arylamidrazones 57 and diethyl azodicarboxylate 58.…”

mentioning

confidence: 99%

Synthesis of Biologically Relevant 1,2,3- and 1,3,4-Triazoles: From Classical Pathway to Green Chemistry

2021

View full text Add to dashboard Cite

Green Chemistry has become in the last two decades an increasing part of research interest. Nonconventional «green» sources for chemical reactions include micro-wave, mechanical mixing, visible light and ultrasound. 1,2,3-triazoles have important applications in pharmaceutical chemistry while their 1,2,4 counterparts are developed to a lesser extent. In the review presented here we will focus on synthesis of 1,2,3 and 1,2,4-triazole systems by means of classical and « green chemistry » conditions involving ultrasound chemistry and mechanochemistry. The focus will be on compounds/scaffolds that possess biological/pharmacophoric properties. Finally, we will also present the formal cycloreversion of 1,2,3-triazole compounds under mechanical forces and its potential use in biological systems.

show abstract