Domino Michael/retro-Michael/Mukaiyama-aldol reactions of 1,3-bis-silyl enol ethers with 3-acyl- and 3-formylbenzopyrylium triflates - Synthesis of functionalised 2,4'-dihydroxybenzophenones

被引：45

作者：

Appel, Bettina

Rotzoll, Sven

Kranich, Remo

Reinke, Helmut

Langer, Peter

机构：

[1] Ernst Moritz Arndt Univ Greifswald, Inst Biochem, D-17487 Greifswald, Germany

[2] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[3] Revotar Biopharmaceut AG, D-16761 Hennigsdorf, Germany

[4] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 16期

关键词：

benzophenones; cyclisations; chromones; domino reactions; silyl enol ethers;

D O I：

10.1002/ejoc.200600082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1,3-bis-silyl enol ethers with 3-acyl- and 3formylbenzopyrylium triflates, which can be generated in situ from 3-acyl- and 3-formylchromones, affords a great variety of functionalised 2,4'-dihydroxybenzophenones and 4-(2-hydroxybenzoyl)salicylates. These products are formed by a domino Michael/retro-Michael/Mukaiyama-aldoI reac- tion. This methodology is successfully applied to the synthesis of novel UV-A/B and UV-B filters. Three 4-(2-hydroxybenzoyl)salicylic acids show a good in vitro activity in a selectin bioassay. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

引用

页码：3638 / 3644

页数：7

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[1] Synthesis and structure-activity relationships of 2-vinylchroman-4-ones as potent antibiotic agents [J].