ISSN 1070-3632, Russian Journal of General Chemistry, 2008, Vol. 78, No. 6, pp. 1277–1282. © Pleiades Publishing, Ltd., 2008. 1277 Synthesis and Spectral Studies of Pyranone Derivative and Its Cu(II), Co(II), Ni(II) and Zn(II) Complexes 1 E. Akbas a , M. Sonmez a , B. Anıl b , and F. Aslanoglu a a Department of Chemistry, Faculty of Science and Arts, Yuzuncu Yil University 65080, Van, Turkey b Department of Chemistry, Faculty of Science and Arts, Ataturk University 25240, Erzurum, Turkey e-mail: esvakbas@hotmail.com Received April 12, 2007 Abstract—Under the thermolysis condition, 5-phenyl-2,3-dihydro-2,3-furandione (IV) in inert aprotic sol- vents as p-xylene at 130–140°C yields 3-benzoyl-4-hydroxy-6-phenyl-2H-pyran-2-one (VI) via phenyl ketene (V). The compound (VI) was converted into the corresponding 3-benzoyl-4-hydroxy-6-phenylpyridin-2(1H)- one (VII), and 3-benzoyl-2-oxo-6-phenyl-2H-pyran-4-yl acetate (VIII), by its reactions with ammonium hydroxyde, and acetic anhydride, respectively. On the other hand, a series of new various metal complexes (IX- XIa, XIb) of VI was synthesized. The results suggest that the compound VI as bidentate ligand indicate a binuclear structure for the Cu(II) complex with square-planar geometry. The Ni(II) and Zn(II) complexes are of tetrahedral and the Co(II) complex is also octahedral geometry with water molecules at the axial positions. The structures of compounds and complexes were characterized on the basis of elemental analysis, Mass, IR, 1 H, and 13 C NMR spectra. α-Oxoketenes are often used as structure particles in chemical design. Usually they can not be stabilized under reaction conditions. The most common method for the synthesis of these highly reactive molecules is the thermolysis of 2,3-dihydrofuran-2,3-diones and 1,3-dioxan-4-ones [1–7]. The ketenes usually were added to multiple bond systems via a [2+2] process across their C=C as well as C=O double bonds, while α-oxoketenes show a pronounced behavior to form [4π+2π] hetero-Diels Alder adducts when trapped with dienophiles. When the reaction is carried out in an inert medium, the –COC=C part of ketene molecule acts as heterodiene while the C=C bond of ketene acts as heterodienophile [7–11]. The nucleophilic addition is one of the most characteristic reactions of the ketenes [10–13, 15]. N- acrylamides of aroylacetic acids were obtained by the reaction of the arylketenes with aromatic and heterocyclic amines [16]. The reactions of ketene with 1,1-diamines form the substituted 6-aryl-2-methylene- 4H-pyrimidin-4-ones [12]. The ketenes towards carbon- nucleophiles converted into 4-pyrone derivative [10]. Besides, the compounds containing pyranone ring are known as good complexing agents and therefore are of interest in coordination and bioinorganic chemistry [17–18]. The interests in these complex derivatives are due to the possibility of their enzyme inhibitory properties [19]. Herein we have reported synthesis of 3-benzoyl-4- hydroxy-6-phenyl-2H-pyran-2-one [11] in inert aprotic solvent. Thereafter, 3-benzoyl-4-hydroxy-6-phenyl-2H- pyran-2-one was converted into the corresponding 3- benzoyl-4-hydroxy-6-phenylpyridin-2(1H)-one, and 3- benzoyl-2-oxo-6-phenyl-2H-pyran-4-yl acetate, by its reactions with ammonium hydroxyde, and acetic an- hydride, respectively. In addition the new Cu(II), Co(II), Ni(II) and Zn(II) metal complexes of the 3-benzoyl-4- hydroxy-6-phenyl-2H-pyran-2-one (VI) were synthe- sized and characterized. The reactions of oxalyl chloride with a solution of alkenyloxysilanes in dry ether at room temperature gives 2,3-furandiones (I). They undergo decom- position, by heating to a temperature near the melting DOI: 10.1134/S1070363208060315 1 The text was submitted by the authors in English.