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

被引：11

作者：

Chen, Po-Yuan ^{[1
]}

Chen, Hsing-Ming ^{[2
]}

Chiang, Michael Y. ^{[3
]}

Wang, You-Feng ^{[1
]}

Li, Sie-Rong ^{[1
]}

Wang, Tzu-Pin ^{[1
]}

Wang, Eng-Chi ^{[1
]}

机构：

[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan

[2] Fooyin Univ, Dept Nutr & Hlth Sci, Kaohsiung 831, Taiwan

[3] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 807, Taiwan

来源：

TETRAHEDRON | 2012年 / 68卷 / 14期

关键词：

Isovanillin; Tandem reaction; o-Oxiranylmethylbenzonitriles; 3,4-Dihydroisoquinolin-1(2H)-one; BISCHLER-NAPIERALSKI; BETA-ARYLETHYLISOCYANATES; CYCLIZATION; LYCORICIDINE; INHIBITORS; BENZAMIDES; CONCISE; ROUTE;

D O I：

10.1016/j.tet.2012.02.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3030 / 3036

页数：7

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