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Paper | Regular issue | Vol 31, No. 1, 1990, pp.67-78
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5125
Fluorinated Analogues of the Imidazole Insect Growth Regulator KK-42

César Arbonés, Francisco J. Sánchez, Maria-Pilar Marco, Francisco Camps, and Angel Messeguer*

*Departmenr of Biological Chemistry, C.I.D. (CSIC), J. Giroba 18. 08034-Barcelona, Spain

Abstract

The preparation of compounds 1b, 1c and 1e, monofluoro and trifluoromethyl analogues of the imidazole KK-42 (1a) is reported. The synthetic sequence involves the formation of an imine between the appropriate fluoro aldehyde and benzylamine, followed by condensation with tosylmethyl isocyanide (TosMIC) in basic media. Each step has been thoroughly studied and the whole procedure has been optimized for the case of model imidazole 1a. It has been observed that when possible, the imine formation proceeds with a concomitant Z/E isomerization on the olefin moiety of the α,β-unsaturated system. Finally, data on the biological activity of the title compounds as ecdysone antagonists are also presented.