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Nucleophilic Vinylic Substitution in Perfluoroacylchromenes. Diastereoselective Synthesis of Push–Pull Enamino Ketones
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2021-09-06 , DOI: 10.1134/s1070428021070046
V. A. Osyanin 1 , K. S. Korzhenko 1 , D. A. Rashchepkina 1 , D. V. Osipov 1 , Yu. N. Klimochkin 1
Affiliation  

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.



中文翻译:

全氟酰基色烯中的亲核乙烯基取代。推拉烯氨基酮的非对映选择性合成

摘要

2-全氟-1的反应ħ -苯并[ ˚F ]色烯和6,7-二甲基-3-三氟乙酰基-4- ħ色烯与脂族伯胺和氨,得到一系列烯氨基酮的含有(2-羟基萘-1- -基)甲基或2-羟基苄基取代基在羰基的α-位。这些反应涉及吡喃环的打开,随后是氮杂-迈克尔加成作为初始步骤。发现获得的烯氨基酮作为单一的E异构体存在于 DMSO 溶液中。

更新日期:2021-09-07
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