4‐Phosphonated or 4‐Free 1,2,3‐Triazoles: What Controls the Dimroth Reaction of Arylazides with 2‐Oxopropylphosphonates?
Nazariy T. Pokhodylo, Olga Ya. Shyyka, Evgeny Goreshnik, Мыкола Д. Обушак
Abstract
Abstract The influence of base‐solvent systems and substituents on the reaction of aryl azides with dimethyl 2‐oxopropylphosphonate was studied. It was shown that azides with electron‐withdrawing substituents in K 2 CO 3 /DMSO medium (mild conditions) afford 5‐methyl‐1‐aryl‐1 H ‐1,2,3‐triazole‐4‐ylphosphonates as major products. In contrast, azides with electron‐donating substituents produce 1‐aryl‐5‐methyl‐1 H ‐1,2,3‐triazoles. Based on the obtained results the plausible mechanisms of the reactions were discussed and key points of selectivity control were indicated.
Topics & Concepts
ArylChemistrySelectivitySolventMedicinal chemistryBase (topology)TriazoleCombinatorial chemistryOrganic chemistryCatalysisMathematicsMathematical analysisAlkylClick Chemistry and ApplicationsChemical Synthesis and AnalysisSynthesis and Catalytic Reactions