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Facile synthesis of polynuclear heterocycles and acyclic C-nucleosides via á-substituted cinamonitrile (II)

Kh.M.Abu-zied, H.A.R.Hussein, A.A.Abu-Hashem

2-Amino-3-cyanothiophene derivative (II) react with formic acid, and carbon disulphide to afford the newly constructed derivatives (1) and (2) respectively. Compound (1) formthe corresponding 4-hydrazino derivative (4) after its chlorination followed by the treatment of the formed 4-choloroderivative with hydrazine hydrate (99%).While the 2- hydrazino-derivative (6) was obtained upon the methylation of compound (2) withmethyl iodide followed by reacting the collected 2-methylthio-derivative (5) with hydrazine hydrate (1:3; 99%). The S-glycosides are produced when 2, 4-dithione derivative 2´ reacted with 2’,3’,4’, 6’-tetra-O-acetyl-â-D-gulcopyranosyl or galactopyranosyl bromide in dry acetone with stirring at room temperature to afford (7a,b). The acyclic C-nucleosides (12a-c) and (13a-c) were obtained when 2- and 4- hydrazino derivatives reacted with aldo-sugars either aldohexsoses or aldopentoses such as D- glucose, D-galactose and Dxylose.