Base-induced transformations of ortho-nitrobenzylketones: intramolecular displacement of nitro group versus nitro-nitrite rearrangement

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• 作者：Sergey I. Filimonov^a ; ^{filimonovsi@ystu.ru} ; Zhanna V. Chirkova^a ; ^&dagger ; ; Igor G. Abramov^a ; ^&dagger ; ; Sergey I. Firgang^b ; ^&Dagger ; ; Galina A. Stashina^b ; ^&Dagger ; ; Yuri A. Strelenko^b ; ^&Dagger ; ; Dmitriy V. Khakimov^b ; ^&Dagger ; ; Tatyana S. Pivina^b ; ^&Dagger ; ; Alexander V. Samet^b ; ^&Dagger ; ; ^{sametav@server.ioc.ac.ru} ; Kyrill Yu. Suponitsky^c ; ^§ ;
• 关键词：4-Bromo-5-nitrophthalonitrile ; 4-(2-R-2-Oxoethyl)-5-nitrophthalonitriles ; 1 ; 2-Benzoxazole-5 ; 6-dicarbonitriles ; Alkyl 5 ; 6-Dicyanobenzofuran-2-carboxylates ; 1-Hydroxyindole-5 ; 6-dicarbonitriles ; Nitro-nitrite rearrangement
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：29 July, 2012
• 年：2012
• 卷：68
• 期：30
• 页码：5991-5997
• 全文大小：411 K

文摘

Reactions of 4-bromo-5-nitrophthalonitrile (BNPN) with enolates of alkyl 4-R-2,4-dioxobutanoates gave alkyl 3-acyl-5,6-dicyanobenzofuran-2-carboxylates, 4-(2-R-2-oxoethyl)-5-nitrophthalonitriles, or 3-acyl-1,2-benzoxazole-5,6-dicarbonitriles. With a base, 4-(2-R-2-oxoethyl)-5-nitrophthalonitriles either undergo nitro-nitrite rearrangement resulting in 3-acyl-1,2-benzoxazole-5,6-dicarbonitriles or yield 2-R-benzofuran-5,6-dicarbonitriles with a nitro group displacement.