Haloacetylated enol ethers: 15. Study of the regiochemistry of the cyclo‐condensation of β‐alkoxyvinyl trihalomethyl ketones with N‐methyl thiourea

Abstract

AbstractA study of the regiochemistry of the cyclo‐condensation reaction of ß‐alkoxyvinyl trihalomethyl ketones with an unsymmetric dinucleophile N‐methyl thiourea to afford a series of 1‐methyl‐3‐(4,4,4‐trifluoro[chloro]‐3‐oxo‐1‐butenyl)thioureas and the corresponding N‐methyl pyrimidinethione derivatives is reported. The absolute assignment of the position of the N‐methyl group in the pyrimidine ring was obtained through a nmr study based on two dimensional HMBC and NOESY experiments.