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Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK-917 01 Trnava, Slovak Republic
Institute of Chemistry, Karl-Franzens University of Graz, A-8010 Graz, Austria
* Author to whom correspondence should be addressed.
Received: 20 October 2003; in revised form: 14 January 2004 / Accepted: 15 January 2004 / Published: 31 January 2004
Abstract: 4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results show that microwave irradiation shortens the reaction times while affording comparable yields. Elementary analysis, UV, IR and 1D NMR proved the structure of new synthesised compounds. 2D NMR spectroscopic measurements confirmed that the configuration at the carbon-carbon double bond corresponds to the pure E isomers of the products.
Keywords: 5-Arylfuran-2-carboxaldehydes; furo[3; 2-b]pyrrole-2-carboxaldehydes; furo- [2; 3-b]pyrrole-2-carboxaldehydes; hippuric acid; microwave irradiation; 1; 3-oxazol- 5(4H)-ones; furo[3; 2-b]pyrrole-5-carboxylates; furo[2; 3-b]pyrrole-5-carboxylates; 1H- and 13 C-NMR; COSY; NOESY; HSQC; HMBC.
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Puterová, Z.; Sterk, H.; Krutošíková, A. Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid. Molecules 2004, 9, 11-21.
Puterová Z, Sterk H, Krutošíková A. Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid. Molecules. 2004; 9(1):11-21.
Puterová, Zita; Sterk, Heinz; Krutošíková, Alžbeta. 2004. "Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid." Molecules 9, no. 1: 11-21.