An Efficient Synthesis of New Substituted Spiro Pyrazolethieno, Pyrimidinethieno, and Benzodiazepinethieno Pyridazine Derivatives with Biological Activities

Abstract

3-Ethyl 2-amino-4-methyl-5-phenyl thiophene carboxylate 1 was used as a starting material to synthesize 2a,b via coupling with malononitrile or acetyl acetone, respectively. When heated, under reflux in sodium ethoxide solution, 2a,b give 3a,b. On the other hand, when compounds 3a,b were heated under reflux in ethanol with hydrazine hydrate, thiourea, or 1,1-phenylenediamine hydrochloride and a catalytic amount of piperidine 4a,b, 5a,b and 6a,b, were produced, respectively. The new compounds were tested for their antimicrobial activity. Compounds 2a–6b showed antibacterial activities, and 2a,2b and 4b showed antifungal activities.

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Keywords:

• Antibacterial
• antifungal
• benzodiazepinethieno-pyridazine
• biological activity
• pyrimidinethieno
• spiro pyrazolethieno