Nucleophilic Vinylic Substitution in Perfluoroacylchromenes. Diastereoselective Synthesis of Push–Pull Enamino Ketones

Abstract

The reactions of 2-perfluoroacyl-1H-benzo[f]chromenes and 6,7-dimethyl-3-trifluoroacetyl-4Hchromene 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.

Synthesis, Thermal, DFT Calculations, HOMO-LUMO, MEP, and Molecular Docking Analysis of New Derivatives of Imidazolin-4-Ones

“…The exocyclic double bond proton C=CH has a chemical shift of about 9 ppm. The coupling constant 3 J = 13.2 Hz [19] for compounds 2a and 2b that exists between the exocyclic vinyl proton C-H and the amino proton N-H lead to the suggestion of the trans relation between these two hydrogens about the C-N bond which acquires partial double character due to conjugation. However, this vinylic C-H appears as a singlet in the case of 2c caused by the fast exchange of the proton of the amine group.…”

“…The lig2 (2b) shows better binding energy to HMGCS protein, suggesting that phenyl substituent is better than methyl and butyl substituents in lig1 (2a) and lig2 (2b). Visualization is done on Discovery Studio [19] of lig1 (2a), lig2 (2b), and lig3 (2c) and they are depicted in Fig. 4, 5 and 6, respectively.…”