The reaction of acyclic α, β-unsaturated β-amino ketones (1) with thiocyanogen was investigated. (1) (R
3=H) reacted with thiocyanogen in 1, 2-dichloroethane at 0°C to give corresponding α, β-unsaturated α-thiocyanato-β-amino ketone (2) in 7883% yield. In contrast, the reaction of α, β-unsaturated β-monosu-bstituted amino ketones (1) (substituent R
3 : Me and Ph) with thiocyanogen at 025°C gave corresponding cyclization products, 2-imino-3, 4, 5-trisubstituted 4-thiazolines (4) in 4488% yield. The reaction of 3-anilino-3-penten-2-one (1) with thiocyanogen at 30°C for 5 hours gave (4c) (41%yield) and 5-acetyl-2-anilino-4-methylthiazole (5) (30% yield), which was the isomerization product of (4c). (4) and 2-amino-4, 5-disubstituted thiazoles (3) were obtained also by cyclization of (2) by heat, acid and alkali in 83100% yield. The structure of (2) was also discussed.
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