Reactions of 3-substituted 5-Arylmethylene-1,3-Thiazolidin-2,4-diones with Azide and Cyanide Ions

Abstract

3-substituted-5-arylmethylene-1,3-thiazolidine-2,4-diones 3a–e react- ed with sodium azide to afford pyrazolinone derivatives 8a–d as well as 5-(4-chlorophenylmethylene)-1,3 - thiazolidine-2,4-dione 7a in the case of 3d and 5-(4-methoxyphenylmethylene-1,3-thiazolidin-2,4-dione 7b as a sole product in the case of 3e . Reactions of potassium cyanide with 3b–d gave butyronitrile derivative 9 as well as 7a and a water soluble adduct that, upon treatment with chloroacetic acid, yielded 10 in the case of 3c and 3d . Also, the treatment of 3e with potassium cyanide afforded a mixture of 7b , but-3-enonitrile derivative 11 and 10 . Structures of all products were elucidated by microanalytical and spectral data.

Keywords:

• 5-arylmethylene-1,3-thiazolidin-2,4-diones
• 2-oxo-but-3-enonitrile
• butyronitrile derivative
• pyridazine derivatives
• pyrazolinone derivatives