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

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

Full description

Saved in:
Bibliographic Details
Published inRussian journal of organic chemistry Vol. 57; no. 7; pp. 1053 - 1062
Main Authors Osyanin, V. A., Korzhenko, K. S., Rashchepkina, D. A., Osipov, D. V., Klimochkin, Yu. N.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.07.2021
Springer Nature
Springer Nature B.V
Subjects
Aliphatic amines
Ammonia
Carbonyl groups
Carbonyls
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Isomers
Ketones
Organic Chemistry
Physical Sciences
Science & Technology
Stereoselectivity
ammonia
perfluoroacylchromenes
enamino ketones
aza-Michael reaction
primary aliphatic amines
nucleophilic vinylic substitution
BASES
NMR-SPECTROSCOPY
FTIR
O-QUINONE METHIDES
REACTIVITY
CHEMISTRY
Online AccessGet full text

Cover

More Information
Summary:The reactions of 2-perfluoroacyl-1 H -benzo[ f ]chromenes and 6,7-dimethyl-3-trifluoroacetyl-4 H -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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428021070046