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The reaction of amino-imidazoles, -pyrazoles and -triazoles with α,β-unsaturated nitriles

✍ Scribed by Sergey A. Komykhov; Konstantin S. Ostras; Alvard R. Kostanyan; Sergey M. Desenko; Valery D. Orlov; Herbert Meier

Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
131 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

The reactions of α,β-unsaturated nitriles (1, 9, 12) as bielectrophiles with aminoazoles (2, 4, 6) as binucleophiles were investigated. Acrylonitrile (1) reacts almost exclusively in a chemoselective Michael-type addition yielding the substituted azoles 3, 5 and 7, respectively. Cinnamonitriles 9a,b behave in a similar way, but the free CN group adds a second molecule 4 yielding 10a,b and its cyclocondensation product 11a,b as minor component. The attempted formation of azolopyrimidines is best achieved by the reaction of the benzylidenemalononitriles 12a -f with 2 or 4. The process is chemo-and regioselective. The structure determinations were based on NMR measurements including DEPT, COSY, ROESY, HMQC and HMBC techniques and correct earlier suggestions.

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