DABCO-Catalyzed Easy Access to Benzo[d]naphtho[2,3-g][1,3]-oxazocine‑8,13(6H,14H)‑diones in Aqueous Media

Document Type : Research Article

Authors

1 Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, I.R. IRAN

2 Department of Medicinal Chemistry, Faculty of Pharmacy & Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, I.R. IRAN

3 Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, I.R. IRAN

4 Department of Chemistry, Imam Hossein University, Tehran, I.R. IRAN

Abstract

An eco-friendly, highly efficient, and tandem reaction between 2-hydroxy-1,4-naphthoquinone and quinolinium salts in the presence of DABCO, 1,4-diazabicyclo[2.2.2]octane, in an aqueous medium is developed for the synthesis of functionalized polycyclic naphthooxazocines. The advantageous features of this operationally simple procedure along with good to excellent yields of products highlighted this method for the preparation of oxazocine. Moreover, the products obtained without the need for column chromatography. In order to reduce the hazards of chemicals and solvents, the reaction was conducted in the green solvent, water. All newly synthesized compounds were characterized by different methods involving IR, 1H NMR, 13C NMR spectroscopy.

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