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

Investigation of the Regiochemistry and Synthetic Studies of the 2,4-Disubstituted Imidazoles via [3 + 2] Annulation Reaction of O-tosylamidoximes with 3-Dimethylaminopropenones.

范振頡(Fan Zhen-Jie)

指導教授 ： 簡敦誠

國立臺灣師範大學/理學院/化學系/碩士(2017年)

https://doi.org/10.6345/NTNU202202487

摘要

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。

關鍵字

三氯化鐵 ； 酸催化 ； [3+2]合環反應 ； 區域選擇性 ； 咪唑

並列摘要

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.

並列關鍵字

1,3dipolarophile ； regiochemistry ； O-Tosyl Amide Oxime

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