Unexpected Spiroproducts from the Reaction of N‐Benzoylglycine with Ortho‐Formylbenzoic Acids −3,5′‐Dioxo‐2′‐Phenyl‐1,3‐Dihydrospiro[Indene‐2,4′‐[1,3]Oxazol]‐1‐yl Acetates: Establishments of Their Structure |
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Authors: | Aryan Younesi Ludmila N Sorotskaya Gennady D Krapivin |
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Institution: | Department of Organic Chemistry, Kuban State University of Technology, Moskovskaya str., 2, 350072 Krasnodar, Russian Federation |
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Abstract: | This paper describes a method of preparation of new 3,5′‐dioxo‐2′‐phenyl‐1,3‐dihydrospiroindene‐2,4′‐1,3]oxazol]‐1‐yl acetate and its 5‐chloro‐ and bromoderivatives as products of interaction of N‐benzoylglycine (hippuric acid) with corresponding ortho‐formylbenzoic acids. The reaction carried out in acetic anhydride media in the presence of piperidine as catalyst. The novel spirocompounds were purified by column chromatography from multicomponent reaction mixtures. The composition of the spiro‐products was confirmed by C, H, N element analysis. The structure was established by IR, MS, 1H‐ and 13C‐NMR analysis including COSY 1H‐13C experiments. |
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Keywords: | N‐Benzoylglycine (hippuric acid) ortho‐Formylbenzoic acid 3 5′ ‐Dioxo‐2′ ‐phenyl‐1 3‐dihydrospiro[indene‐2 4′ ‐[1 3]oxazol]‐1‐yl acetate |
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