Strategy for the synthesis of 2,2-disubstituted 8-azachromanones via Horner-Wadsworth-Emmons olefination

被引：0

作者：

Omelian, Taras V. ^{[1
,2
]}

Ostapchuk, Eugeniy N. ^{[1
,2
]}

Dobrydnev, Alexey V. ^{[1
,2
]}

Malets, Yehor S. ^{[1
,3
]}

Brovarets, Volodymyr S. ^{[3
]}

Grygorenko, Oleksandr O. ^{[1
,2
]}

机构：

[1] Enamine Ltd, 78 Chervonotkatska St, UA-02094 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, 60 Volodymyrska St, UA-01601 Kiev, Ukraine

[3] Natl Acad Sci Ukraine, VP Kukhar Inst Bioorgan Chem & Petrochem, 1 Murmanska St, UA-02094 Kiev, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2020年 / 56卷 / 02期

关键词：

azachromanone; phosphonate; cyclization; Horner-Wadsworth-Emmons reaction; olefination; protecting group; NAD(+)-DEPENDENT DNA-LIGASE; DERIVATIVES; AMLEXANOX; INHIBITION; CARBANIONS; PROGRESS; SAR;

D O I：

10.1007/s10593-020-02646-z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2,2-disubstituted 8-azachromanones, including spirocyclic compounds, have been synthesized via Horner-Wadsworth- Emmons reaction. Dimethyl methylphosphonate was acylated with methyl 2-methoxypyridine-3-carboxylate to afford the key intermediate - dimethyl [2-(2-methoxypyridin-3-yl)-2-oxoethyl]phosphonate. Further reaction of this phosphonate and ketones followed by treatment with TMSCl-NaI provided the target 8-azachromanones. Scope and limitations of the developed synthetic method have been investigated.

引用

页码：213 / 218

页数：6

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