Hetero-Diels-Alder Reaction of Phosphorylated Nitroso Alkenes with Enol Ethers on Water: A Clean Approach Toward 1,2-Oxazine Derivatives

被引：33

作者：

de los Santos, Jesus M. ^{[1
]}

Ignacio, Roberto ^{[1
]}

Es Sbai, Zouhair ^{[1
]}

Aparicio, Domitila ^{[1
]}

Palacios, Francisco ^{[1
]}

机构：

[1] Univ Basque Country, Ctr Invest & Estudios Avanzados Lucio Lascaray, Fac Farm, Dept Quim Organ 1, Vitoria 01006, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 16期

关键词：

ORGANIC-REACTIONS; ASYMMETRIC-SYNTHESIS; 6-SILOXY-SUBSTITUTED 5,6-DIHYDRO-4H-1,2-OXAZINES; ALPHA; BETA-UNSATURATED OXIMES; BETA-AMINOPHOSPHONATES; CONJUGATE PHOSPHINYL; EFFICIENT SYNTHESIS; 4+2 CYCLOADDITIONS; AQUEOUS-MEDIA; CHEMISTRY;

D O I：

10.1021/jo501339c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and eco-friendly synthesis of highly fiinctionalized 1,2-oxazines from phosphinyl- and phosphonyl-nitroso alkenes has been developed. The key step of this process, which involves a two-step sequence of reactions on-water, is a regioselective hetero-Diels Alder cycloaddition reaction of enol ethers to 4-phosphinyl or 4-phosphonyl nitroso alkenes mediated by water itself. The process has also been performed under solvent-free conditions and in organic solvents for comparison.

引用

页码：7607 / 7615

页数：9

共 39 条

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[2] Synthesis of 1,2-oxazine N-oxides via noncatalyzed hetero-Diels-Alder reactions of nitroalkenes (microreview)
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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1949 - 1980
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (10) : 1515 - 1518
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de los Santos, Jesus M.
Ignacio, Roberto
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[6] A NOVEL MICHAEL REACTION OF SILYL ENOL ETHERS VIA HETERO-DIELS-ALDER REACTION WITH ALKYLIDENE-MELDRUMS ACID
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Krystyna Bogdanowicz-Szwed
Monatshefte für Chemie - Chemical Monthly, 2008, 139 : 647 - 655
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