Research On The Reactions Of 1-Benzoyl-3-Arylthiourea Derivatives And α-Halogen Carbonyl Compounds

Our team has developed a new route to synthesize imidazoline (or iinidazole)-2-thione derivatives. Based upon the results obtained, we proposed a possible mechanism, in which the reaction may involved the formation of an intermediate - a-halocarbonyl compound.The aim of this thesis was to testify the possibility of the mechanism, to design and synthesize the new imidazoline (or imidazole)-2-thione derivatives. In initial experiments, we succeeded in preparation of three series of compounds (3a~f, 4a~f and 6a~6f) by treating -bromoacetophenone, 1-bromoacetone with l-benzoyl-3-arylthioureas, the structure of products were confirmed by spectral data. It had been proven that the reactions went via the a-halocarbonyl compounds. On the basis of the results obtained, we carried out the reaction of 1,3-dichloroacetone and l-benzoyl-3-arylthioureas, and succeeded in preparation of two series of compounds (7a~7f and 8a~8f), the results were consistent with our anticipation. Then, the reaction was been extended to chloroacetyl chloride, and a new class of compounds named l-benzoyl-3-aryl-5-imidazolidinone-2-thiones (9a~9f) were obtained, its mechanism is different from the previous mentioned. The structure of 9a~9f were characterized by 1HNMR, 13CNMR, IR and MS spectra. Furthermore, we explored the reactions of 1,1-dichloroacetyl chloride, 1,1,1-trichloroacetyl chloride, oxalyl chloride and l-benzoyl-3-arylthioureas, some interesting results were obtained, at the same time, the significance of the research was also described in context.