Nucleophilic Vinylic Substitution in Perfluoroacylchromenes. Diastereoselective Synthesis of Push–Pull Enamino Ketones
V. A. Osyanin, Кирилл С. Корженко, Daria A. Rashchepkina, Dmitry V. Osipov, Yu. N. Klimochkin
Abstract
The reactions of 2-perfluoroacyl-1H-benzo[f]chromenes and 6,7-dimethyl-3-trifluoroacetyl-4H-chromene with primary aliphatic amines and ammonia afforded a series of enamino ketones containing a (2-hydroxynaphthalen-1-yl)methyl or 2-hydroxybenzyl substituent in the α-position with respect to the carbonyl group. These reactions involved opening of the pyran ring, which followed aza-Michael addition as the initial step. The obtained enamino ketones were found to exist in DMSO solution as single E isomers.
Topics & Concepts
ChemistrySubstituentRing (chemistry)PyranKetoneNucleophilic substitutionMedicinal chemistryCarbonyl groupSubstitution reactionAmmoniaNucleophileOrganic chemistryCatalysisSynthesis of Indole DerivativesSynthesis of Organic CompoundsSynthesis of heterocyclic compounds