Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furans

被引：38

作者：

Crawford, KR ^{[1
]}

Bur, SK ^{[1
]}

Straub, CS ^{[1
]}

Padwa, A ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 18期

关键词：

D O I：

10.1021/ol035233k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Intramolecular cyclization reactions of 5-halo- and 5-nitro-substituted furanylamides were examined. The 2-alkoxy-5-bromofuran derivative 2 produced the rearranged dihydroquinone 6 (36%), a product from the rearrangement of the intermediate oxabicycle 3. The 5-halo substituted furoyl amide 18 was converted to the polyfunctional oxabicycle 20 in 82% yield and at a much faster rate than the unsubstituted furanyl system 17. The 5-nitro-substituted furfuryl amide 33b underwent an unusual isomerization-cyclization reaction under microwave conditions to provide 1,4-dihydro-2H-benzo[4,5]furo[2,3-c]pyridin-3-one 34.

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页码：3337 / 3340

页数：4

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