A. Lyčka, S. Lun̆ák, T. Aysha
Jun 9, 2010
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Influential Citations
19
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 15 N-Labelled ethyl 5-oxo-2-phenyl-4-(2-phenylhydrazono)-4,5-dihydro-1 H -pyrrole-3-carboxylate was synthesized by azo-coupling of diazotized aniline (using Na 15 NO 2 , 99% 15 N) with ethyl 4,5-dihydro-5-oxo-2-phenyl-(1 H )-pyrrole-3-carboxylate. The product was formed as a tautomeric hydrazone mixture as confirmed by 13 C and 15 N chemical shifts, and was obtained as a mixture of E and Z isomers according to n J ( 15 N, 13 C). A comparison of the 1 H NMR data with GIAO DFT calculations enabled determination of the configuration of the carboxy ester group in both isomers.