探討O-tosylamidoximes與3-Dimethylaminopropenones進行[3 + 2]合環反應之區域選擇性及合成2,4-Disubstituted Imidazoles之研究

Abstract

本研究探討O-tosylalkylamidoximes與作為1,3-dipolarophile Michael Acceptors的3-dimethylaminopropenones在路易士酸FeCl3催化下進行[3 + 2]合環反應合成2,4-disubstituted imidazoles和2,4,5-trisubstituted imidazoles。 此外，本研究亦探討反應之區域選擇性，製備N-substituted- O-tosylamidoximes此一氮上含烷類取代基之起始物與Michael Acceptors進行反應，純化並透過2-D NMR NOESY鑑定其烷類取代基接在產物imidazole之氮上相對位置，結果推論具高區域選擇性，也藉此暫時推測出其反應機制。A [3+2] cycloadditon type of process for the iron-catalyzed synthesis of 2,4-disubstituted imidazoles and 2,4,5-trisubstituted imidazoles from O-Tosyl Amide Oximes and 3-dimethylamino-1-propenone as a 1,3-dipolarophile Michael acceptor has been achieved. In order to explore the reaction mechanism and regiochemistry, we synthesized N-substituted-O-tosyl amide oximes as a starting material then the study clarified the regioselectivity and the scope was explored with many substrates. Moreover, the substituted imidazole derivatives are valuable in treatment of many systemic fungal infections.