An investigation into the alkylation of 1,2,4-triazole

Azoles as Reactive Nucleophiles with Cyclic Perfluoroalkenes

“…Previously, it had been shown that alkylation of 1,2,4-triazole proceeded mainly with the formation of the N 1 -substituted species with smaller amounts of the N 4 -alkylated triazole depending upon the alkylating agent. [24] The presence of a nitrogen atom, which has a nonbonded pair of electrons, adjacent to the N 1 position in tri-A C H T U N G T R E N N U N G azole enhances the nucleophilicity. [25] However, higher ring strain in the case of i and j increases the reactivity of the fluorine atom attached to the double bond; thus the carbocation formed in the reaction can readily bond to both the N tene-1-amine, [26] and 3-dimethylamino-4-[(pentacarbonylchromium)(dimethylamino)carbenyl]-6,6,7,7-tetrafluoro-2,4-diazabicycloA C H T U N G T R E N N U N G [3.2.0]hepta-1(5),2-diene.…”

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…Amines have been converted into 1-formyl semicarbazides 199, which were cyclized smoothly to 2,4-dihydro-3H-1,2,4-triazolin-3-ones 200 with hexamethyldisilazane (HMDS), bromotrimethylsilane, and a catalytic amount of ammonium sulfate (Scheme 12.67) [242]. [250]. Sodium hydroxide [251], sodium methoxide [252], and sodium hydride [253] are other bases that have been successfully employed in these reactions.…”

Regioselective alkylation of 1,2,4-triazole using ionic liquids under microwave conditions

“…We came across some literature reports [13] suggesting that the alkylation reaction of 1,2,4-triazole generally lead to the formation of two isomers, and as one of the isomers is water soluble, so it might disappear during aqueous work up. Hence, we performed a non-aqueous work up of the reaction mixture, and proton NMR of the product suggested that only one of the isomers was formed, which further confirmed the regioselectivity of the developed method.…”

“…Supporting information: Full experimental details, 1 H and 13 C NMR spectral data of synthesized compounds, and ionic liquids can be found with the online version of this article.…”