A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN

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• 作者：Po-Yuan Chen^a ; Hsing-Ming Chen^b ; Michael Y. Chiang^c ; You-Feng Wang^a ; Sie-Rong Li^a ; Tzu-Pin Wang^a ; Eng-Chi Wang^a ; ^{enchwa@kmu.edu.tw}
• 关键词：Isovanillin ; Tandem reaction ; o-Oxiranylmethylbenzonitriles ; 3 ; 4-Dihydroisoquinolin-1(2H)-one
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：8 April, 2012
• 卷：68
• 期：14
• 页码：3030-3036
• 文件大小：346 K

摘要

A novel synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones is described. o-Oxiranylmethylbenzonitriles, prepared from isovanillin via five synthetic steps, were treated with NaCN/tetra-n-butylammonium bromide (TBAB) to yield 3,4-dihydroisoquinolin-1(2H)-ones in good yields. This one pot reaction demonstrates the novel and chemoselective nature of ring-opening of epoxide by cyanide to generate an iminoisochroman ring via cyclization, again ring-opening by cyanide to generate a Michael acceptor and a donor, and ring re-cyclization through an intramolecular conjugate addition. The detailed mechanism is also rationally proposed.