Synthesis of 1,2,3‐Triazoles from Azide‐Derivatised Aminocyclitols by Catalytic Diazo Transfer and CuAAC Click Chemistry

Abstract

AbstractCuII‐catalysed diazo transfer and CuI‐catalysed azide–alkyne 1,3‐dipolar cycloaddition (CuAAC) “click chemistry” were used to synthesis C7N aminocyclitol‐derivatised 1,2,3‐triazoles. In the course of this work, the ‐N=N‐ moiety was transferred onto C7N aminocyclitols such as validamine, valienamine and valiolamine by employing imidazole‐1‐sulfonyl azide as the diazo transfer reagent with catalysis by CuII, ZnII and NiII, in moderate to good yields. The obtained azidocyclitols were coupled with various terminal alkynes under modified Meldal's conditions with good to excellent yields. The stereo‐ and regiochemistry of the products were confirmed by 2D‐NMR (NOESY and HMBC). One‐pot syntheses of the corresponding 1,2,3‐triazoles, as safer and more efficient procedures, were also investigated and gave moderate to good yields.