Synthesis and Some Chemical Transformations of Unsaturated Ketones of the Dihydropyran Series

被引：0

作者：

Shatirova, M. I. ^{[1
]}

Gusiyev, N. Kh. ^{[1
]}

Aliyev, A. G. ^{[1
]}

Nagiyeva, Sh. F. ^{[1
]}

机构：

[1] Azerbaijan Natl Acad Sci, Inst Polymer Mat, Sumgait, Azerbaijan

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 55卷 / 09期

关键词：

unsaturated ketones; dihydropyran series; epoxy ketones; amino epoxy ketones; aldolization-crotonization; biologically and physiologically active compounds; DERIVATIVES;

D O I：

10.1134/S1070428019090069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methods have been developed for the synthesis of unsaturated ketones of the dihydropyran series via aldolization-crotonization of 3,4-dihydro-2H-pyran-2-carbaldehyde with some unsaturated ketones. Among the proposed methods, the optimal were reactions carried out in 20% alcoholic sodium hydroxide at room temperature, which ensured higher selectivity, high yield (85-95%) of the target products, and minimization of side processes. The obtained unsaturated ketones were subjected to various chemical transformations involving the side-chain double bond, and their new derivatives were synthesized. In particular, the oxidation of unsaturated ketones with 28% hydrogen peroxide gave the corresponding epoxy ketones which reacted with secondary amines to afford amino alcohols.

引用

页码：1299 / 1304

页数：6

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