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Synthesis 2007(6): 824-828  
DOI: 10.1055/s-2007-965934
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (Z)-2-(2H-Isoquinolin-1-ylidene)acetamides by Iodine-Mediated Cyclization of (Z)-3-Amino-3-(2-vinylphenyl)propenamides

Kazuhiro Kobayashi*, Kenichi Hashimoto, Taiyo Shiokawa, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 27 October 2006
Publication Date:
13 February 2007 (online)

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Abstract

(Z)-2-(2-Acetyl-2H-isoquinolin-1-ylidene)acetamides have been synthesized from 2-vinylbenzonitrile derivatives in three steps. The key step involves the iodine-mediated 6-endo cyclization of (Z)-3-acetylamino-3-(2-vinylphenyl)propenamides, which are prepared by the coupling of 2-vinylbenzonitriles with magnesium enolates of tertiary amides followed by N-acetylation.

Key words

6-endo cyclization - iodine - isoquinoline - magnesium amide - magnesium enolate

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