1,3-dipolar Cycloaddition-initiated Reactions For The Synthesis Of Privileged Polyheterocyclic Compounds

Pyrrolidine and its derivatives are widely existed in biological natural and synthetic pharmaceutical molecules,such as antibacterial drugs quinolones,antihypertensive drugs barnidipine,hypoglycemic drugs vildagliptin and the intermediate of anti-tumor drugs Voreloxin topoisomerase II inhibitor are all containing the pyrrolidine scaffold.Therefore,the wide range of pharmacological potentials of these bioactive molecules have attracted lots of synthetic and medicinal chemists to explore facile routes for making the desired products.The subject in this thesis is foucs on [3+2] cycloaddition-initiated reactions in combination with different post-condensation modifications for making biological potential priviledged heterocyclic compounds.The research contents of this thesis are as follows:(1)Intermediates generated from three-component [3+2] cycloaddition of2-bromobenzaldehydes and maleimides with amino esters or amino acids underwent N-propargylation/intramolecularreductive Heck cyclization to form a series of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines.The stereochemistry of final products was confirmed by 2D-NOESY analysis.(2)A novel and efficient approach for the synthesis of triazolobenzodiazepine analogs by employing tetrahydropyrrolo[3,4-c]pyrrole-1,3-dione as the substrates,which is via sequential N-propargylation,Cucatalyzed Huisgen [3+2] cycloadditon and N-arylation reactions.