2016 IEEE International Conference on Systems, Man, and Cybernetics, SMC 2016 - Conference Proceedings.
Institute of Electrical and Electronics Engineers Inc..
2017.
P. 3051-3056
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
Number of issue
3
Language
English
Pages
1517-1528
Status
Published
Link
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
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Journal of Physics: Conference Series.
Institute of Physics Publishing.
Vol. 788.
2017.