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

✍ Scribed by Nilo Zanatta; Claudia Da C. Madruga; Patricia Da C. Marisco; Darlene C. Flores; Helio G. Bonacorso; Marcos A. P. Martins

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 344 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370531

✦ Synopsis

Abstract

A 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.