✍ Scribed by Moon-Kook Jeon; Kyongtae Kim; Sung Hoon Kim
No coin nor oath required. For personal study only.
The reactions of N,N-(di-n-alkyl)-N'-arylthiocarbamoylamidines (1) with 2-bromo-l-phenylethanone in the presence of K2CO3 in TI-IF at reflux gave 3-(di-n-alkylamino)-2-arylimino-5-phenyl-2H-1,4-thiazines (7) in 32 to 62 % yields. Treatment of compounds 1 with bromoacetyl bromide in the presence of pyridine in CH2C12 at 0 °C afforded 5-(di-n-alkylamino)-6-arylimino-2H-1,4-thiazin-3ones (12) in 41 to 84 % yields, whereas the same reactions of 1 with 2-bmmopropionyl bromide under the same conditions gave 4-(di..n-alkylamino)-5-arylimino-2-(l-bromoethylidene)-2H-thiazolines ( ) as minor compounds in addition to thiazin-3-ones 16, analogous to compounds 12. The reactions of 1 with ethyl bromoacetate in CH2C12 at room temperature, however, gave [(arylimino)(Sethoxycarbonyhnethyl)lmethyl-N,N-(di-n-propyl)amidine hydmbromides (19) in 71 to 88 % yields. Compounds 7, 16, 17, and 19 are all new and the mechanisms of their formations are proposed.
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