Journal
TETRAHEDRON
Volume 64, Issue 22, Pages 5055-5060Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.03.065
Keywords
2-hydroxyacetophenones imines; nitroalkenes; Michael addition; 4-methyl-2H-chromenes; trihalomethylated compounds
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The reaction of N-unsubstituted imines of 2-hydroxyacetophenones with trichloro(trifluoro)ethylidene nitromethanes in the presence of DABCO proceeds via tandem oxa-Michael/aza-Henry additions (in dichloromethane) or aza-Michael addition (in benzene) to give 4-methyl-3-nitro-2-trichloro(trifluoro)-methyl-2H-chromenes or 1,1,1-trichloro(trifluoro)-3-nitro-N-[1-(2-hydroxyaryl)ethylidene]propan-2-amines, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
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