Reaction of Push-Pull Enaminoketones and in Situ Generated ortho-Quinone Methides: Synthesis of 3-Acyl-4H-chromenes and 2-Acyl-1H-benzo[f]chromenes as Precursors for Hydroxybenzylated Heterocycles

A simple and efficient method for the synthesis of 4H-chromenes and 1H-benzo[f]chromenes containing a trifluoroacetyl or aroyl group in the pyran ring from o-quinone methide precursors and push-pull enaminoketones has been developed. The chromenes are presumably formed through an initial oxa-Diels-Alder reaction, followed by an elimination of amine. The possibility of further transformations of given chromenes to o-hydroxybenzylated pyrazoles, isoxazoles, and pyridines has been demonstrated. © 2017 American Chemical Society.

Authors
Lukashenko A.V.1 , Osyanin V.A. 1, 2 , Osipov D.V.1 , Klimochkin Y.N.1
Journal
Journal of Organic Chemistry
Number of issue
3
Language
English
Pages
1517-1528
Status
Published
Link
External link
DOI
10.1021/acs.joc.6b02716
Volume
82
Year
2017
Organizations
  • 1 Department of Organic Chemistry, Chemical Technological Faculty, Samara State Technical University, 244 Molodogvardeyskaya St., Samara, 443100, Russian Federation
  • 2 Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
Keywords
Chemistry; Organic compounds; Diels-Alder reaction; Enaminoketones; Heterocycles; Isoxazoles; nocv1; O-quinones; Push pull; Pyrazoles; Quinone methides; Photochemical reactions; acetic anhydride; chromene derivative; ketone derivative; Mannich base; quinone derivative; xylene; Article; benzylation; carbon nuclear magnetic resonance; cycloaddition; deamination; electrophilicity; Michael addition; nucleophilicity; precursor; proton nuclear magnetic resonance; regioselectivity; stereospecificity; synthesis
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/5625/
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