Synthesis of 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines from 3-nitro-2-(trifluoromethyl)-2H-chromenes and aminoenones derived from acetylacetone and cyclic amines

TETRAHEDRON LETTERS

卷:54

Article

Korotaev, Vladislav Yu.¹  Barkov, Alexey Yu.¹  Sosnovskikh, Vyacheslav Ya.¹ 

[1] Ural Fed Univ, Dept Chem, Ekaterinburg 620000, Russia

关键词: 3-Nitro-2H-chromenes;    Push-pull enamines;    Michael addition;    Chromanes;    Chromeno[3,4-b]pyridines;   

DOI  :  10.1016/j.tetlet.2013.03.137

来源: Elsevier

【 摘 要 】

Reactions of 3-nitro-2H-chromenes with aminoenones derived from acetylacetone and cyclic amines proceed diastereoselectively to give functionalized 2,3,4-trisubstituted chromanes as a result of nucleophilic addition of the vinylogous beta-methyl group at the C-4 atom of the chromene system. From these compounds, under acidic conditions, 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines and 4-acetoacetonyl-3-nitro-2-(trichloromethyl/phenyl)chromanes, depending on the substituent at the 2-position, were obtained in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

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