A convenient synthesis of 2-azido and 2-thiocyanato-2,3-unsaturated cyclic ketones

BOZ M., ZAİM Ö., Esen H.

Turkish Journal of Chemistry, cilt.33, sa.1, ss.59-65, 2009 (SCI-Expanded, Scopus, TRDizin) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 33 Sayı: 1
  • Basım Tarihi: 2009
  • Doi Numarası: 10.3906/kim-0811-12
  • Dergi Adı: Turkish Journal of Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.59-65
  • Anahtar Kelimeler: 1,2-Cyclic diketones, Azides, Deoxygenation, Enols, Thiocyanates
  • Trakya Üniversitesi Adresli: Evet

Özet

2-Azido and 2-thiocyanato-2,3-unsaturated ketones were synthesized by utilizing functionalization of 5- or 6-membered cycloalkane-1,2-diones, namely diosphenols, with dimethylthiocarbomoyl chloride, which activates the system towards reaction with nucleophiles in acidic conditions. Replacement of the enolic oxygen of the diosphenols with azide and thiocyanate may be achieved by treating their dimethylthiocarbamates with sodium azide or potassium thiocyanate in boiling acetonitrile/acetic acid. © TÜBİTAK.