Base-Mediated Cyclization Reaction of 2-(5-Hydroxy-1-pentynyl)benzonitriles to 4-Amino-2,3-dihydronaphtho[2,3-b]furanes and Synthesis of Furanonaphthoquinones

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• 作者：Chih-Jyun Tsai ; Chin-Chau Chen ; Chih-Wei Tsai ; Ming-Jung Wu
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：81
• 期：9
• 页码：3882-3889
• 全文大小：360K
• 年卷期：0
• ISSN：1520-6904

文摘

An efficient transformation of 2-(5-hydroxy-1-pentynyl)benzonitriles 5 to furanonaphthoquinones 11 is presented. Treatment of 5 with 1.5 equiv of NaOMe in DMSO at 140 °C for 0.5 h gave 6 in good yields. Conversion of 6 to 11 was carried out by oxidation of 6 with Fremy’s salt and KH₂PO₄ in acetone and water, followed by dehydrogenation using palladium on charcoal in diphenylether at reflux temperature.