Domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylalkylidene)malononitriles: synthesis of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans and a rare case of [1,5] sigmatropic shift of the nitro group

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• 作者：Vladislav Yu. Korotaev ; Alexey Yu. Barkov ; Vyacheslav Ya. Sosnovskikh
• 关键词：3-Nitro-2-(trifluoromethyl)-2H-chromenes ; 1 ; 1-Dicyanoolefins ; 6-(Trifluoromethyl)-6H-dibenzo[b ; d]pyrans ; Domino reaction ; [1 ; 5] Sigmatropic nitro-shift
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：18 November, 2013
• 年：2013
• 卷：69
• 期：46
• 页码：9642-9647
• 全文大小：670 K

文摘

A variety of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans were easily synthesized in good yields under mild conditions by a domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylethylidene)- and 2-(1-phenylpropylidene)malononitriles. In the latter case, intermediate 7-amino-10-methyl-10-nitro-9-phenyl-6-(trifluoromethyl)-10,10a-dihydro-6H-benzo[c]chromene-8-carbonitriles were isolated as a result of a rare [1,5] sigmatropic shift of the nitro group.