The Synthesis Of Novel Carbonylthiourea, Amide, Imidazo-[2, 1-b]-1, 3, 4-thiadiazole Containing Pyrazole Ring

Many chemical workers were interested in the latest research which approved that ultrasound and microwave could not only improve reaction conditions, but also speed-up reaction and increase chemical yield.In recent years, there has been increasing interest in synthesis of heterocyclic compounds that have biological and commercial importance. Pyrazole are biological interesting molecules and their chemistry is receiving considerable attention due to antisepsis, antiphlogistic, plant growth regulate and anti-platelet aggregation. It is the important position of compounds containing pyrazole in agricultural chemical and pharmacological research field that attract more and more people's interest. In addition, 1,3,4-thiadiazole, carbonylthiourea, amide, 1,2,4-triazole and imidazo[2,1-b]-1,3,4-thiadiazole are associated with a particularly strong biological property, and have received considerable attention over the past years. In order to realize combination of multiform active ingredients, we designed and have synthesized novel compounds of carbonylthiourea, amide, imidazo[2,1-b]-1,3,4-thiadiazole which containing pyrazole ring. It extended the research field of such compounds and provided abundant leading compounds for later selecting work of effective drugs. This thesis consists of two major parts:The first part is about literature review. The progress in application and synthesis of pyrazole, 1,3,4-thiadiazole, carbonylthiourea, amide, 1,2,4-triazole and imidazo[2,1-b]-1,3,4- thiadiazole and the application of ultrasound and microwave in organic synthesis were systematic exposition.The second part is about experimental content. It introduces our major work:1 Synthesis under ultrasound radiation and biological activity of carbonylthiourea containing pyrazole and thiadiazole ring.2 Synthesis of amide containing pyrazole and thiadiazole ring under microwave radiation.3 Synthesis of novel imidazo[2,1-b]-1,3,4-thiadiazole containing pyrazole and 1,2,4- triazole ring under ultrasound radiation.The innovations of the thesis are based on the follows:1 A series of unreported N-[5-(1-phenyl-3-methyl-5-chloropyrazol-4-yl)-1,3,4-thiadiazol -2-yl]-N′-carbonylthiourea have been synthesized by means of ultrasonic radiation method. The preliminary activity tests showed that the compound has activity of inhibitting tumor cell growth.2 A series of unreported N-(2-alkyl-1,3,4-thiadiazol-5-yl)-N′-(1-phenyl-3-methyl-5-chlo- ro/phenoxylpyrazol-4-yl)-carbonylthiourea have been synthesized by means of ultrasonic radiation method. Its crystal structure determined by the X-ray diffraction. The preliminary activity tests showed that the compound has activity of inhibitting tumor cell growth.3 A series of unreported N-[5-(1-phenyl-3-methyl-5-chloropyrazol-4-yl)-1,3,4-thiadiazol -2-yl]-aroylamine have been synthesized by the reaction of 2-amino-5-(1-phenyl-3-methyl-5- chloropyrazol-4-yl)-1,3,4-thiadiazole with aroylchlorides under microwave radiation method.4 2-amino-5-(1-phenyl-3-methyl-5-chloro/phenoxylpyrazole-4-yl)-1,3,4-thiadiazole have been prepared by reaction of 1-phenyl-3-methyl-5-chloro/ phenoxylpyrazole-4-formylic acid with aminothiourea in the presence of phosphorus oxychloride. Then a series of unreported 2-(1-phenyl-3-methyl-5-chloro/phenoxylpyrazol-4-yl)-5-(1,2,4-triazol-1-yl)-6- aryl-imidazo[2,1-b]-1,3,4-thiadiazole were synthesized by reaction of the thiadiazole withω-bromo-ω-(1H-1,2,4-triazol-1-yl)acetophenones by means of ultrasonic radiation method and conventional method.