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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
Author(s) -
Younesi Aryan,
Sorotskaya Ludmila N.,
Krapivin Gennady D.
Publication year - 2009
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200900092
Subject(s) - chemistry , hippuric acid , acetic anhydride , piperidine , indene , acetic acid , column chromatography , organic chemistry , medicinal chemistry , catalysis , nuclear chemistry , chromatography , urine , biochemistry
Abstract This paper describes a method of preparation of new 3,5′‐dioxo‐2′‐phenyl‐1,3‐dihydrospiro[indene‐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, 1 H‐ and 13 C‐NMR analysis including COSY 1 H‐ 13 C experiments.