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Synthesis 2006(17): 2934-2938  
DOI: 10.1055/s-2006-950186
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of 1,4-Disubstituted Isoquinolines by Reactions of α-Substituted 2-Lithio-β-methoxystyrenes with Nitriles

Kazuhiro Kobayashi*, Kazutaka Hayashi, Kazuna Miyamoto, 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 13 April 2006
Publication Date:
15 August 2006 (online)

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Abstract

It has been found that halogen-lithium exchange between α-substituted 2-bromo-β-methoxystyrene derivatives and n-butyllithium generates α-substituted 2-lithio-β-methoxystyrene derivatives, which successfully react with a range of nitriles to afford the corresponding 1,4-disubstituted isoquinolines in reasonable yields.

Key words

benzyl anion - isoquinoline - nitrile - organolithium - styrene

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8

A possibility of the formation of 3 via 6π electrocyclization of 4 followed by elimination of lithium methoxide cannot be excluded.