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Please login to access the full content or check if you have access via15.6.1.1.1.1.4.2.4 Method 4: From 2-(2-Ethoxyvinyl)benzonitrile
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Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 852.
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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Meeeeeeeeee-8(8M)-eee (88, M8 = M); Meeeeee Meeeeeeee:[88]
M eeeeeee ee 8-(8-eeeeeeeeeee)eeeeeeeeeeee (8.8 e, 8.88 eeee), 8 M ee Me8MM8 (88 eM), 88% M8M8 (88 eM), eee eeeeeee (88 eM) eee eeeeeee ee ee eee 8 e. Meeee eeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeee eeee M8M eee eeeeeeeee eeee MMMe8. Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeee (eeeeee) ee eeee 88 (M8 = M); eeeee: 8.88 e (88%); ee 888–888°M.
M eeeeeee ee eee eeeee (88, M8 = M; 8.8 e, 8.88 eeee), MeMM (88 ee), eee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeeee eee 8 e. Meeee eeeeeeeeeee ee eee eeeeeee, eee eeeeeee eee eeeeeeeeeee eeeeeee ee Me8MM8 eee MMMe8. Mee eeeeeee eeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeee (eeeeeee); eeeee: 8.88 e (88%); ee 888–888°M.
References
[40] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[41] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) M 8e, 888.