Facile Formation of 1, 3-Disubstituted 2, 3, 5, 6-Tetrahydro-2-thioxopyrimidin-4 (1H)-ones and 2-N, 3-Disubstituted 2, 3, 5, 6-Tetrahyro-2-imino-1, 3-thiazin-4-ones from Thioureas and β-Haloacyl Halides

Abstract

The reaction of 1, 3-disubstituted thioureas (1) with β-haloacyl halides (2) was carried out in 5% NaOH-CH₂Cl₂ to afford 1, 3-disubstituted 2, 3, 5, 6-tetrahydro-2-thioxopyrimidin-4 (1H)-ones (3) or 2-N, 3-disubstituted 2, 3, 5, 6-tetrahydro-2-imino-1, 3-thiazin-4-ones (4) in yields of 51-63 or 54-68%, respectively.