Research On The Synthesis Of Ferrocenyl Chalcone

Because of their unique structures, ferrocene and its derivatives have manyspecial properties, and they have been used in many areas, such as catalysis,assistant combustion reagents, medicine, et al. In recent years, thiadiazolecompounds showed more pronounced activity in pesticides and they can be usedas fungicides, plant growth regulators, insecticides and herbicides. Therefore,these compounds present have drawn an increasing research interest as a “greenpesticide”. There were many reports on the synthesis and application offerrocence derivatives and1,3,4-thiadiazole heterocyclic compoundsrespectively,whereas few on the introducing ferrocene group into1,3,4-thiadiazole compounds. Therefore, in order to make the family of1,3,4-thiadiazole compounds become more complete and look for1,3,4-thiadiazole heterocyclic compounds containing ferrocene group withbiological activities, a series of new compounds of different subsituent groupswere synthesized.Ferrocenyl chalcone are one kind of important ferrocene derivations, theyare one important intermediate of organic synthesis, they have shown goodbiological activities against several types of bacteria, tumor and pinworm.Ferrocenylchalcone usually synthesized in solution under conventional heatingmethod. However, there are long reaction time, many by-products, low yield,danger and high cost in solvent reaction. Solvent-free reaction in organicsynthesis had been widely used at home and abroad in recent years. Meanwhile,the operation and post-processing was simplified and the reaction time wasshortened. Some solvent-free reaction can be realized by a simple grindingoperation. Their interesting applicantion attracted us to continue our previousstudies. In this paper, two series of ferrocenylchalcone have been synthesized.The following three aspects have been mainly undertaken: （1）With KF/Al2O3as catalyst, in the solvent-free conditions,nine ferrocenylchalcone, have been prepared by the condensation of acetylferrocene with ben-zaldehyde, furaldehyde,4-methoxylbenzaldehyde,3-nitrylbenzaldehyde,4-met-hylbenzaldehyde,4-fluorobenzaldehyde,4-chlorobenzaldehyde,4-bromobenzaldehyde,4-dimethyl aminobenzaldehyde. Their structures were characterized byIR,¹HNMR,¹³CNMR and elemental analysis.（2）Six novel benzaldehyde derivatives containing1,3,4-thiadiazole, havebeen prepared by4-fluorobenzaldehyde with2-amino-1,3,4-thiadiazole,2-amino-5-methyl-1,3,4-thiadiazole,2-amino-5-ethyl-1,3,4-thia-diazole,2-amino-5-propyl-1,3,4-thiadiazole,2-amino-5-phenoxyethyl-1,3,4-thiadiazole,2-amino-5-β-naphthyl ethyl-1,3,4-thiadiazole. Their structures were characterized by IR,¹HNMR,¹³CNMR, elemental analysis and UV-Vis.（3）Six novel chalcone derivatives containing ferrocenyl and1,3,4-thiadia-zole, have been prepared by the condensation of acetylferrocene with the sixnovel benzaldehyde derivatives containing1,3,4-thiadiazole. Their structureswere characterized by IR,¹HNMR,¹³CNMR, elemental analysis and UV-Vis.