3-Nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes: synthesis and reactions with nucleophiles

3-Nitro-2-phenyl-2-(trifluoromethyl)-2H-chromenes: synthesis and reactions with nucleophiles

A method is proposed for the synthesis of 3-nitro-2-phenyl-2-(trifluoromethyl)-2 H -chromenes by tandem condensation of salicylic aldehydes with ( E )-3,3,3-trifluoro-1-nitro-2-phenylprop-1-ene in the presence of triethylamine. The example of 3-nitro-2-phenyl-2-(trifluoromethyl)-2 H -chromene was us...

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Veröffentlicht in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2016-10, Vol.52 (10), p.814-822
Hauptverfasser: Barkov, Alexey Yu, Korotaev, Vladislav Yu, Kotovich, Ivan V., Zimnitskiy, Nikolai S., Kutyashev, Igor B., Sosnovskikh, Vyacheslav Ya
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Aniline
Chemical synthesis
Chemistry
Chemistry and Materials Science
Condensates
Nitromethane
Nucleophiles
Organic Chemistry
Pharmacy
Structural analysis
Triethylamine
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Zusammenfassung:A method is proposed for the synthesis of 3-nitro-2-phenyl-2-(trifluoromethyl)-2 H -chromenes by tandem condensation of salicylic aldehydes with ( E )-3,3,3-trifluoro-1-nitro-2-phenylprop-1-ene in the presence of triethylamine. The example of 3-nitro-2-phenyl-2-(trifluoromethyl)-2 H -chromene was used to demonstrate conjugated addition reactions with enamines, nitromethane, and aniline, which are characteristic for this class of compounds. The structure of the obtained products was confirmed by X-ray structural analysis.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-016-1971-y