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Synthesis 2008(18): 2874-2878  
DOI: 10.1055/s-2008-1067235
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (Z)-2-[Quinazolin-4(3H)-ylidene]acetonitriles by the Reaction of N-(2-Cyanophenyl)alkanimidates with 2-Lithioacetonitrile

Kazuhiro Kobayashi*, Takahiro Ukon, Hidenari Nakano, Shuhei Fukamachi, Hisatoshi Konishi
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School 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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Publikationsverlauf

Received 16 April 2008
Publikationsdatum:
22. August 2008 (online)

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Abstract

An efficient preparation of (Z)-2-[quinazolin-4(3H)-ylidene]acetonitriles has been achieved in one pot by addition of 2-lithioacetonitrile to the cyano carbon of N-(2-cyanophenyl)alkanimidates, followed by intramolecular attack of the resulting imino anion on the imidate carbon with loss of alkoxide and subsequent tautomerization.

Key words

carbanions - fused-ring system - heterocycles - nitriles - ring closure - quinazoline

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