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Synthesis 2002(17): 2517-2520
DOI: 10.1055/s-2002-35635
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Polycyano-Substituted Azulenes via Direct Oxidative Cyanation Reaction

Mieczysław Mąkosza*a, Mariusz Kędzioreka, Stanisław Ostrowskib
a Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warszawa, Poland
Fax: +48(22)6326681; e-Mail: icho-s@icho.edu.pl;
b Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland
Fax: +48(25)6442045; e-Mail: stan@ap.siedlce.pl;
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Publication History

Received 31 July 2002
Publication Date:
20 November 2002 (online)

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Abstract

The synthesis of dicyano-, tricyano-, and tetracyanoazulenes substituted on both rings via direct oxidative cyanation reaction is described. 1-Cyanoazulene or 1,3-dicyanoazulene treated with tetraethylammonium cyanide (Et4N + CN - ) and subsequently with DDQ or para-chloranil were transformed stepwise into the desired polycyano-substituted azulenes.

Key words

arenes - cyanoazulenes - cyanation - nucleophilic addition - oxidative substitution.