Reactivity of cyclic sulfamidates towards lithium acetylides: Synthesis of alkynylated amines

ESKİCİ M., Karanfil A., ÖZER M. S., Sarikürkcü C.

Tetrahedron Letters, cilt.52, sa.48, ss.6336-6341, 2011 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 52 Sayı: 48
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1016/j.tetlet.2011.08.171
  • Dergi Adı: Tetrahedron Letters
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6336-6341
  • Anahtar Kelimeler: Cyclic sulfamidates, Nucleophilic substitution, Lithium acetylides, Alkynylated amines
  • Manisa Celal Bayar Üniversitesi Adresli: Evet

Özet

A 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.