Reaction of Pyridine with Phenylcyanoacetylene: A New Route to Functionalized Polyconjugated 1,4-Dihydropyridine Systems

Pyridine reacts with phenylcyanoacetylene under mild conditions (20–25 °C, no catalyst) to unexpectedly give the 2:3 adduct — a C,N‐functionalized polyconjugated 1,4‐dihydropyridine system — containing two 1,4‐dihydropyridine cycles and four vinylene units formed by three molecules of phenylcyanoace...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2006-03, Vol.2006 (6), p.1581-1585
Main Authors: Trofimov, Boris A., Andriyankova, Ludmila V., Mal'kina, Anastasiya G., Nikitina, Lina P., Afonin, Andrei V., Ushakov, Igor A., Sinegovskaya, Lidiya M., Vakul'skaya, Tamara I.
Format: Article
Language:English
Subjects:
Alkynes
Conjugation
Pyridines
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Summary:Pyridine reacts with phenylcyanoacetylene under mild conditions (20–25 °C, no catalyst) to unexpectedly give the 2:3 adduct — a C,N‐functionalized polyconjugated 1,4‐dihydropyridine system — containing two 1,4‐dihydropyridine cycles and four vinylene units formed by three molecules of phenylcyanoacetylene (the yield is up to 46 %). Other products are higher oligomers of phenylcyanoacetylene terminated by 1,4‐dihydropyridine cycles (approx. 30 % yield). Assembly of the 2:3 adduct proceeds regio‐ and stereoselectively — only one of the possible isomers is formed. The oligomers show paramagnetic and electroconductive properties. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200500712