From imidates to vinyl-1,2,4-triazoles: Synthesis, mechanistic aspects and first issues of their reactivity

Investigation of Structure of 3-Methyl-4-(3-benzenesulfonyloxy-4- methoxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one by DFT (B3LYP/mPW1PW91) and HF Methods

“…Molekülün bağ açıları, bağ uzunlukları, dihedral açıları ve mulliken atomi kanalizi gibi önemli parametreleri teorik olarak incelenmiştir. Bununla birlikte moleküle ait titreşim frekansları, 1 H ve 13 C NMR kimyasal kayma değerleri deneysel ve teorik olarak kaydedilmiştir. Bileşiğinin gaz ortamında HOMO ve LUMO enerjileri hesaplanmış ve bu parametrelerden faydalanılarak her bir yöntem için olan ΔE enerji farkları ve elektronik parametreleri tayin edilmiştir.…”

“…Giriş 4,5-Dihidro-1H-1,2,4-triazol-5-on türevli Schiff bazları, potansiyel biyoaktiviteye sahip olan ve yapısında üç azot atomu bulunduran heterosiklik bileşiklerdir. 1,2,4-Triazol türevli bileşikleri geniş spektrumlu aktivitelerinden dolayı tıp ve ilaç alanında yaygın şekilde kullanılmaktadır [1,2]. 1,2,4-Triazol türevli bileşikler, antifungal [3], antibakteriyel [4], antitümör [5], antitripanozomal [6], antiproliferatif [7] ve antibiyotik [8] özelliklere sahip olduğu için klinik tedavide tercih edilmektedir.…”

Design and synthesis of coumarin-triazole hybrids: biocompatible anti-diabetic agents, in silico molecular docking and ADME screening

“…Five-membered heterocycles, specifically, 1,2,4-triazoles plays a pivotal role in medicinal chemistry for their versatile applications. 1,2,4-Triazoles were synthesized by; a cycloaddition of nitriles and amidines in the presence MCM-41/copper(I) complex as heterogeneous catalyst [ 12 ], iodine catalyzed multicomponent reaction of aryl hydrazines, paraformaldehyde, NH 4 OAc, and alcohols under electrochemical conditions [ 13 ], regio-selective synthesis involving Ag(I) catalyzed reaction of ethyl cyanoacetate with aryldiazoniumtetrafluoroborate in water at 0 °C [ 14 ], Iodine catalyzed environmentally benign C–N bond formation from isothiocyanates in water at room temperature [ 15 ], palladium and copper catalyzed arylation of styrene [ 16 ], triflic anhydride activated microwave-induced one-pot synthesis involving secondary amides and hydrazides [ 17 ], and by the reaction of hydrazides with isothiocyanate under optimized reaction conditions [ 18 ] 1,2,4-Triazoles were reported to show DHFR inhibitor [ 19 ], and antimicrobial [ 20 ] activities.…”

Choline Chloride Based Deep Eutectic Solvents as a Tuneable Medium for Synthesis of Coumarinyl 1,2,4‐Triazoles: Effect of Solvent Type and Temperature

“…The ratio of 1,2,4-triazoles and thiosemicarbazides in reaction mixtures was determined by HPLC and 1 H NMR. [29] An effect of different solvents on the formation of triazoles from substituted hydrazines and isothiocyanates, followed by iodine mediated cyclization, was studied by Jiao et al [30] The type of the solvent greatly influenced the reaction rate and product yield, and ethanol was suggested as optimal for this type of reaction. Scheme 1.…”

“…[28] Azzouni et al synthesized 1,2,4-triazoles from acryloylimidates with hydrazines at room temperature in methanol, expanding the possibilities of introducing substituents in positions N(1), C(3) and C(5) of 1,2,4triazole ring. [29] An effect of different solvents on the formation of triazoles from substituted hydrazines and isothiocyanates, followed by iodine mediated cyclization, was studied by Jiao et al [30] The type of the solvent greatly influenced the reaction rate and product yield, and ethanol was suggested as optimal for this type of reaction. The influence of the solvent type on the formation of 1,2,4-triazoles from hydrazines and imides fol-lowed by filtration through Al 2 O 3 was also studied, where DMF was found to be the most convenient and alumina crucial for cyclization into the triazole ring system.…”