Research And Application Of Nitrogen-containing Heterocyclic Allylation Reaction Based On MBH Carbonate

Nitrogenous heterocycles are one of the most important structural components of drugs and are widely found in many natural products and drug molecules.Nallylation of nitrogen-containing heterocycles is an important heterocyclic modification strategy that has received extensive attention from scientists.This paper mainly studies the N-allylation reaction of nitrogen-containing heterocycles involved in Morita-Baylis-Hillman(MBH)carbonate and its application in drug molecules.The first chapter briefly introduces the research progress of N-allylation reaction.The substitution reaction between allylation reagents and nitrogen-containing heterocycles is the most direct and efficient method for synthesizing nitrogenous heterocycles containing allyl structures.In the past,strong alkalis,toxic reagents,and expensive transition metals were required,and there were problems such as harsh reaction conditions and heavy metal residues.MBH carbonate can undergo Nallylation reaction with a variety of nitrogen-containing nucleophiles under mild conditions,which is an efficient and environmentally friendly method for preparing nitrogen-containing heterocycles with various structures containing allyl structures.The second chapter mainly focuses on the N-allylation reaction of 1,4-diazabicyclo[2.2.2]octane(DABCO)catalyzed MBH adducts and benzolactams,and synthesized 38 nitrogen-containing heterocycles containing allyl structures with a yield of 15–100%.This method has a wide range of substrates and mild reaction conditions,which can not only be used for structural modification of drugs,but also further transformation of the final product,which has great application potential in the research and development of new drugs.The third chapter develops a method for generating N-alkyl pyridone with high selectivity using MBH carbonate and pyridone compounds as substrates.DABCO catalyzed the N-allylation of MBH adducts and pyridone compounds at room temperature,and synthesized 23 nitrogenous heterocycles with various structures containing allyl structures at 8–100% yield.The method is easy to operate,has a wide range of substrate applications,and has high chemical selectivity of N/O.In summary,MBH carbonate was used as allylation reagent to undergo nucleophilic substitution reaction with nitrogenous heterocycles,and nitrogenous heterocycles containing allyl structures with diverse structures were synthesized.This method has the advantages of wide range of substrate application,cheap and easy availability of raw materials,simple operation,and mild reaction conditions,and provides a simple,efficient and green method for the synthesis of molecules with multiple structures and potential biological activities.