无金属氧化剂和过渡金属参与的光诱导直接氧化环化 1-芳基-2-(呋喃/噻吩-2-基)丁烷-1,3-二酮。
Oxidant and Transition-Metal-Free Photoinduced Direct Oxidative Annulation of 1-Aryl-2-(furan/thiophen-2-yl)butane-1,3-diones.
机构信息
Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University , Xi'an 710119, People's Republic of China.
出版信息
J Org Chem. 2017 Dec 1;82(23):12097-12105. doi: 10.1021/acs.joc.7b01839. Epub 2017 Nov 2.
A photoinduced direct oxidative annulation of 1-aryl-2-(furan/thiophen-2-yl)butane-1,3-diones and ethyl-2-(furan-2-yl)-3-oxo-3-(aryl-2-yl)propanoates in EtOH without the need for any transition metals and oxidants provided access to highly functionalized polyheterocyclic 1-(5-hydroxynaphtho[2,1-b]furan-4-yl)ethanones and 1-(5-hydroxyfuran/thieno/pyrrolo[3,2-e]benzofuran-4-yl)ethanones. The phenomenon of excited-state intramolecular proton transfer (ESIPT) was observed for both 1-(5-hydroxynaphtho[2,1-b]furan-4-yl)ethanone and 1-(5-hydroxy furan/thieno/pyrrolo[3,2-e]benzofuran-4-yl)ethanone analogues.
在没有任何过渡金属和氧化剂的情况下，通过光诱导直接氧化环化 1-芳基-2-(呋喃/噻吩-2-基)丁烷-1,3-二酮和乙基-2-(呋喃-2-基)-3-氧代-3-(芳基-2-基)丙酸盐在 EtOH 中，可得到高度官能化的多杂环 1-(5-羟基萘并[2,1-b]呋喃-4-基)乙酮和 1-(5-羟基呋喃/噻吩/吡咯并[3,2-e]苯并呋喃-4-基)乙酮。对于 1-(5-羟基萘并[2,1-b]呋喃-4-基)乙酮和 1-(5-羟基呋喃/噻吩/吡咯并[3,2-e]苯并呋喃-4-基)乙酮类似物，都观察到了激发态分子内质子转移（ESIPT）现象。
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