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Studies on nitroenamines. Part III . Synthesis and spectral properties of 4‐Acyl‐1‐arylimidazoles

1987; Wiley; Volume: 24; Issue: 6 Linguagem: Inglês

10.1002/jhet.5570240649

1943-5193

Antonio Gómez-Sánchez, Francisco J. Hidalgo, José Luis Chiara,

Synthesis and Biological Evaluation

Abstract The catalytic (C/Pd) hydrogenation of 3‐arylamino‐2‐nitro‐2‐enones ( 1 ) in the presence of carboxylic ortho esters ( 2 ) affords 4‐acyl‐1‐arylimidazoles ( 3 ) in yields (20–70%) which depend on the degree of substitution of the imidazole ring. The spectral properties of compounds 3 , and particularly the 13 C‐nmr spectra, reflect both the electronic and steric effects of the substituents on the π‐electron delocalization and planarity of the bicyclic system.