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15.6.1.1.1.1.4.2.4 Method 4: From 2-(2-Ethoxyvinyl)benzonitrile

DOI: 10.1055/sos-SD-015-01386

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515852.

Palladium-catalyzed coupling of 2-bromobenzonitrile with ethynyltrimethylsilane and the addition of ethanol, produces 2-(2-ethoxyvinyl)benzonitrile which, after conversion of the nitrile into primary amide 40 (R1=H), closes to isoquinolin-1(2H)-one (41, R1=H) on exposure to acid (Scheme 26).[‌40‌] Similarly, Heck coupling of 2-iodobenzonitrile with ethyl 2-ethoxyacrylate forms a comparable enol ether, and its corresponding primary amide 40 (R1=CO2Et) closes with acid to an isoquinolin-1(2H)-one with a 3-ester group (41, R1=CO2Et).[‌41‌]

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