Synthesis and biological activity of some heterocyclic systems containing anthraquinone.

2-Aminoanthraquinone (1) was reacted with ethyl chloroformate to afford 2. The reaction between carbamate 2 and hydrazine hydrate gave semicarbazide 3, which on treatment with benzoic acid, phenyl isothiocyanate and carbon disulfide/potassium hydroxide furnished oxadiazoles 4, 6 and triazole 5, respectively. Also, treatment of 1 with chloroacetyl chloride gave chloroacetyl derivative 8. The reaction of glycolic acid, thioglycolic acid, diethyl malonate and malononitrile with 8 has been investigated. Compound 8 was treated with potassium thiocyanate to give 12, which was cyclized to 13a, while the reaction between 8 and potassium cyanate gave 13b directly. The structures of hitherto unknown compounds were confirmed by analytical and spectral methods. Some of the synthesized compounds were screened to test their antibacterial and antifungal properties.