Mesut BOZ, Ömer Zaim And Hilal ESEN, Ömer ZAİM, Hilal ESEN

10686

A Convenient Synthesis of 2-Azido and 2-Thiocyanato-2,3-Unsaturated Cyclic Ketones

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.
Anahtar Kelimeler:

Azides, thiocyanates, enols, deoxygenation, 1, 2-cyclic diketones

A Convenient Synthesis of 2-Azido and 2-Thiocyanato-2,3-Unsaturated Cyclic Ketones

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.
Keywords:

Azides, thiocyanates, enols, deoxygenation, 1, 2-cyclic diketones,

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Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
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