Title of article
Stereoselective hetero-Diels–Alder reaction of 3-nitro-2-trihalomethyl-2H-chromenes with 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions
Author/Authors
Vladislav Yu. Korotaev، نويسنده , , Vyacheslav Ya Sosnovskikh، نويسنده , , Mikhail A. Barabanov، نويسنده , , Evgeniya S. Yasnova، نويسنده , , Marina A. Ezhikova، نويسنده , , Mikhail I. Kodess، نويسنده , , Pavel A. Slepukhin، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2010
Pages
6
From page
1404
To page
1409
Abstract
3-Nitro-2-trifluoro(trichloro)methyl-2H-chromenes undergo heterodiene cycloaddition to 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions producing novel cyclic nitronates with high stereoselectivity and in good yields. 3,6-Dinitro-2-trifluoromethyl-2H-chromene reacts with two molecules of ethyl vinyl ether to give the tandem [4+2]/[3+2] cycloaddition adduct in 48% yield. The stereochemistry of the products was established based on 2D COSY, NOESY, HSQC, and HMBC experiments and an X-ray diffraction study.
Keywords
3-Nitro-2-trihalomethyl-2H-chromenes , enol ethers , hetero-Diels–Alder reaction , 1 , 3-dipolar cycloaddition , X-ray diffraction study , NMR spectroscopy
Journal title
Tetrahedron
Serial Year
2010
Journal title
Tetrahedron
Record number
1100565
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