α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones.
Copper(I)-catalyzed alkyne-azide 1,3-cycloaddition reaction (CuAAC, Sharpless-Meldal reaction) of various α-azido ketones such as substituted 2-azidoacetophenones, 2-azidobenzosuberone and 3-azido(thio)chromanones with terminal alkynes was studied. The reaction resulted in the formation of the expected 1,2,3-triazoles in moderate to good yields although the reactivity was somewhat lower than in the case of simple azides. Reaction of ethynylchromones as alkynes gave interesting dichromonoid systems bridged by a triazole unit.
Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen, 4010, Hungary.
Krisztina
K
Kónya
Szabolcs
S
Fekete
Anita
A
Abrahám
Tamás
T
Patonay
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D002867:Chromones / Q000737:chemistry*; D057930:Click Chemistry / Q000379:methods*; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D001386:Azides; D002867:Chromones; D007659:Ketones; D014230:Triazoles; D001554:Benzene