Please use this identifier to cite or link to this item: http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100133
Title: 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.
Authors: 簡敦誠
Chien, Tun-Cheng
范振頡
Fan, Zhen-Jie
Keywords: 三氯化鐵
酸催化
[3+2]合環反應
區域選擇性
咪唑
iron(III) chloride
[3+2]cycloaddition
imidazole
1
3dipolarophile
regiochemistry
O-Tosyl Amide Oxime
Issue Date: 2017
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.
URI: http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=%22http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060442057S%22.&%22.id.&
http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100133
Other Identifiers: G060442057S
Appears in Collections:學位論文

Files in This Item:
There are no files associated with this item.


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.