Eskici M.Karanfil A.Özer M.S.Sarikürkcü C.2024-07-222024-07-22201118733581http://akademikarsiv.cbu.edu.tr:4000/handle/123456789/17942A synthetically useful level of reactivity of cyclic sulfamidates toward acetylides is described. Ring-opening reactions of a structurally diverse set of 1,2-and 1,3-cyclic sulfamidates with a range of lithium acetylides from aliphatic, cyclic, aromatic, heteroaromatic, and functionalized alkynes proceed smoothly in a regioselective manner to give the corresponding N-sulfate intermediates. Hydrolysis of these intermediates under acidic conditions furnishes the alkynylated amines in yields ranging from 29% to 98%. The scope of the acetylenic substitution reaction with the structural variations in both the cyclic sulfamidates and alkynes is briefly examined. © 2011 Elsevier Ltd. All rights reserved.Englishalkyne derivativeaminelithium acetatelithium acetylideunclassified drugalkynylationarticlechemical analysischemical structurehydrolysisring openingsynthesisArticle10.1016/j.tetlet.2011.08.171