A NON-ACYL AZIDE ROUTE TO ISOQUINOLIN-1(2H)-ONE DERIVATIVES VIA β-STYRIL CARBAMATES

被引：8

作者：

Chen, Chien-Chang ^{[1
]}

Chen, Li-Yueh ^{[1
]}

Lin, Rung-Yuan ^{[1
]}

Chu, Che-Yi ^{[1
]}

Dai, Shenghong A. ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem Engn, Taichung 40227, Taiwan

来源：

HETEROCYCLES | 2009年 / 78卷 / 12期

关键词：

Isoquinolin-1(2H)-one; beta-Styril Carbamate; Phenylacetaldehyde; Enol Ether of Benzyl Ketone; Non-Chlorine Route; RING EXPANSION; REARRANGEMENT; EPOXIDES; ALDEHYDES; ACIDS;

D O I：

10.3987/COM-09-11800

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The efficient reactions of the phenyl acetaldehydes la-e and the enol ethers of benzyl ketones 1o-s with ethyl urethane lead to the formation of the beta-styril carbamates 2, which are excellent precursors for generating isoquinolin-1(2H)-ones 4. Upon thermolysis at 230 degrees C in an inert organic solution, the carbamates decomposed into the transient beta-styril isocyanate intermediates 3. The resulting isoquinolin-1(2H)-ones obtained were in good yields (65-93%). This synthetic methodology allows the convenient preparation of isoquinolin-1 (2H)-ones via a non-phosgene and non-acyl azide route from readily accessible starting materials.

引用

页码：2979 / 2992

页数：14

共 36 条

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