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■ Synthesis, ¹H and ¹³C NMR Spectra, and Configurational Assigment of Furfurylideneimidazolinones

Peter Schuisky, Wolfgang Twistel, and Spiros Grivas*

*Department of Organic Chemistry, Södertörn University College, Karolinska Institutet, Novum Research Park, SE-141 57 Huddinge, Sweden

Abstract

The title compounds (14 and 15) were obtained by the condensation of a 2- or 3-furaldehyde derivative (prepared from 2-methylfuran) with 2-amino-1-methyl-2-imidazolin-4-one (6) or 5-one (7). Most products from 6 contained the (E)- and (Z)-isomers in comparable amounts; in those from7, the (Z)-isomer generally predominated. The isomers were distinguished by their ¹H and ¹³C NMR spectra, in particular by the three-bond coupling between the carbonyl carbon and the olefinic hydrogen. This led to configurational reassignment of some previously reported analogues.