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Paper | Regular issue | Vol 78, No. 12, 2009, pp.2979-2992
Published online, 15th September, 2009
DOI: 10.3987/COM-09-11800
A Non-Acyl Azide Route to Isoquinolin-1(2H)-one Derivatives via β-Styril Carbamates

Chien-Chang Chen, Li-Yueh Chen, Rung-Yuan Lin, Che-Yi Chu, and Shenghong A. Dai*

*Department of Chemical Engineering, National Chung-Hsing University, Taichung, 40227, Taiwan, R.O.C.

Abstract

The efficient reactions of the phenyl acetaldehydes 1a-e and the enol ethers of benzyl ketones 1o-s with ethyl urethane lead to the formation of the β-styril carbamates 2, which are excellent precursors for generating isoquinolin-1(2H)-ones 4. Upon thermolysis at 230 °C in an inert organic solution, the carbamates decomposed into the transient β-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.