The synthesis and chemoselective study of a novel series N-methyl-2-methylthio-tetrahydropyrimidines and or N-methyl-2-methylthiodihydropyrimidines, from the cyclocondensation reaction of b-alkoxyvinyl trihalomethyl ketones (enones) with 1,2-dimethylisothiourea sulfate is described. It was found that the chemoselectivity depends on both the reaction conditions and the steric and electronic effects of the substituents on the enones.
This work describes the synthesis of a novel series of 2-methylsulfanyl-tetrahydropyrimidines, from the cyclocondensation reaction of -alkoxyvinyl trihalomethyl ketones with 2-methyl-2-thiopseudourea sulfate, in good yields. A detailed 1 H-and 13 C-NMR study was performed on the 2-methylsulfanyltetrahydropyrimidines obtained and 3D structures were proposed based on AM1 calculations supported by 1 H NMR coupling constants and NOESY experiments.
The synthesis of a new series of 3-alkoxy-5-hydroxy-5trifluoromethyl pyrrolidin-2-ones 2a-h from the reaction of 1,1,1trifluoro-4-alkoxyalk-3-en-2-ones 1a-h of the general formula F 3 CC(O)C(R 2)=C(R 1)OR, where: R = Me, Et,-(CH 2) 2- ,-(CH 2) 3-; R 1 = H, Me, Ph, p-Me-Ph, p-F-Ph; and R 2 = H, Me,-(CH 2) 2- ,-(CH 2) 3-with sodium cyanide in hydro-alcoholic medium is reported.
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