2-氫茚1,3-二酮和2,3-丁二酸乙酯之磷催化[3+2]環化反應

• Main Author: 林立梓
• Other Authors: 陳焜銘
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/18702059937443823045

碩士 === 國立臺灣師範大學 === 化學系 === 101 === Using phosphine catalyzed [3+2] annulation to obtain functionalized spirocyclic cyclopentenes which has regioselectivity. 1,3-indandione is an important constituent functional group of natural product. And some derived molecules have biological activity. 2-arylidene-1,3-indandione can be obtained by domino Knoevenagel condensation of 1,3-indandione and aromatic aldehyde in a single one-pot operation. At room temperature and under nitrogen atmosphere, 2-arylidene-1,3-indandione with ethyl-2,3-butadienoate dissolved in toluene, and catalyzed by triphenylphosphine, then doing [3+2] annulation. The starting materials are either electron-donating or electron-withdrawing group, the products both have good regioselectivity (up to 5:1) and yields (63-99%). To the best of our knowledge this is the first report for the synthesis of functionalized cyclopentenes using 2-arylidene-1,3-indandione and ethyl-2,3-butadienoate.