Regiospecific Synthesis of 1-Substituted 1,2,4-Triazoles by Reaction of 1,2,4-Triazole with Aldehydes

Abstract

The reactions of 1,2,4-triazole with aldehydes and various acid chlorides provide a convenient, regiospecific route to 1-substituted 1,2,4-triazoles.

Regio- and Enantioselective Synthesis of Azole Hemiaminal Esters by Lewis Base Catalyzed Dynamic Kinetic Resolution

“…Outside of the special cases of aldehydes that form stable hydrates (e.g., formaldehyde, chloral), reports of stable hemiaminal adducts are rare. Nonisolable hemiaminals formed by reversible addition of triazole to aldehydes followed by capping was reported by Smith in 1990 . More recently, Banert disclosed the reversible addition of azide to aldehydes followed by azide trapping .…”

Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2-Azolyl-3,4-dihydroquinazolines on Penicillium digitatum

“…Many 1-substituted imidazole and 1,2,4-triazole compounds are generally prepared by N-alkylations of imidazole and 1,2,4-triazole with alkylating reagents; however, many of these reactions are limited by the simultaneous formation of the unwanted and biologically inactive 2-isomer of imidazoles or 4-isomer of 1,2,4-triazoles . It was reported that 1,2,4-triazole derivatives can be regiospecifically synthesized by addition reactions of 1,2,4-triazole with aldehydes or carbodiimide, and this method was successfully utilized to prepare many novel triazole derivatives. − The aza-Wittig reaction of iminophosphorane provides an efficient way to synthesize various heterocycles. − It has been reported that quinazolines may be prepared efficiently by tandem aza-Wittig reaction of a suitable iminophosphorane, isocyanate, and various nucleophiles . Cyclization was achieved by initial nucleophilic addition of various nucleophiles to the carbodiimide intermediate and further intramolecular Michael addition.…”

A Regiospecific Synthesis of 1-Heterocyclic Substituted 1,2,4-Triazoles via Addition Reaction of 1,2,4-Triazole With Functionalized Carbodiimide

“…[1] It was reported that 1,2,4-triazole derivatives can be regiospecifically synthesized by addition reactions of 1,2,4-triazole with aldehydes and this method was successfully utilized to prepare many novel triazole derivatives. [2][3][4][5] However, there is no report about addition reaction of 1,2,4-triazole with carbodiimide. Recently we provided a facile synthesis of 2-substituted imidazolinones and quinazolinones via tandem aza-Wittig reaction.…”