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

被引：4
|
作者：
Osyanin, V. A. [1 ]
Korzhenko, K. S. [1 ]
Rashchepkina, D. A. [1 ]
Osipov, D. V. [1 ]
Klimochkin, Yu. N. [1 ]
机构：
[1] Samara State Tech Univ, Samara 443100, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 57卷 / 07期
基金：
俄罗斯科学基金会;
关键词：
perfluoroacylchromenes; primary aliphatic amines; ammonia; enamino ketones; aza-Michael reaction; nucleophilic vinylic substitution; O-QUINONE METHIDES; NMR-SPECTROSCOPY; REACTIVITY; CHEMISTRY; BASES; FTIR;
D O I：
10.1134/S1070428021070046
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 alpha-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.
引用
收藏
页码：1053 / 1062
页数：10
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