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Synthesis 2008(4): 584-588  
DOI: 10.1055/s-2008-1032153
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1-Aminonaphthalene-2-carbonitrile Derivatives by the Reaction of 2-Vinylbenzonitriles with 2-Lithioacetonitrile

Kazuhiro Kobayashi*, Kenichi Hashimoto, Takahiro Ukon, Shuhei Fukamachi, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
Further Information

Publication History

Received 3 October 2007
Publication Date:
31 January 2008 (online)

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Abstract

A new and simple method for the preparation of 1-aminonaphthalene-2-carbonitrile derivatives has been developed. When 2-(1-arylethenyl)benzonitriles are treated with 2-lithioacetonitrile, 1-amino-4-aryl-3,4-dihydronaphthalene-2-carbonitriles are obtained in good yields. The reaction of 2-(1-aryl-2-methoxyethenyl)benzonitriles with 2-lithioacetonitrile leads to the formation of 1-amino-4-arylnaphthalene-2-carbonitriles in fair-to-good yields.

Key words

arenes - carbanions - nitriles - ring closure - tandem reaction

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