5-substituted-1,3-cyclohexanedione For The Synthesis Of Nitrogen-containing Heterocyclic Compounds

This paper first describes the main application of1,3-cyclohexanedione in the synthesisof nitrogen containing heterocyclic compounds. And then, two novel chromenopyrimidone,and benzothineoquinolinone were synthesized from5-substituted-1,3-cyclohexanedione.In this work, firstly, nine iminophosphorane derivatives and twenty-one final productschromeno[2,3-d]pyrimidone derivatives were synthesized from5-substituted-1,3-cyclo-hexanedione. The results show that, they not only possess the structure of pyranopyrimidinestructure, but also contain a benzopyran ring and a pyrimidine ring, which is a class ofheterocyclic compounds with potential good physiological and pharmacological activities,and they also have the remarkable effect in anti-virus, anti coagulation, sterilization,especially. The synthesis method offered several advantages including mild reactionconditions, simple operation, high yields. Especially in the last reaction step, the substitutedphenols were directly added into the reaction, after the reaction of iminophosphorane andiso-cyanate without any treatment. As a result, the reaction times were greatly cut down.Therefore, aza-Wittig reaction supplies a new route for the synthesis of novelchromenopyrimidone derivatives.Secondly, ten novel intermediate enamine and ten novel benzothienoquinolinonederivatives were obtained from5-substituted-1,3-cyclohexanedione. It was found that, thefinal products can exhibit strong fluorescence performance, which expects to have somepotential activities in molecular probes. In addition, some compounds which have thesimilar structure with the target compounds give a good performance in anticancer,antibacterial. Therefore, the synthesis of target compounds has an important research valueto find novel nitrogen containing heterocyclic compounds with fluorescence properties ordrug performance. The reaction conditions were modified constantly, changing the catalysts,using water to replace toxic toluene as solvent, environmental pollution reduced. Therefore,this reaction provides a new synthetic method for studying novel benzothienopyrimidinonederivatives.Fifty nitrogen containing heterocyclic compounds were synthesized，and the structuresof which were characterized by IR,1H NMR, MS, single-crystal X-ray diffraction.