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.
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页码：3638 / 3644
页数：7
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