Reactions of 1,1-diary1-2-isopropylidene-3-methylenecyclopropanes with C,N-diarylnitrones and nitrtile oxides

The reactions of unactivated bis(methylene)cyclopropanes with nitrones and nitrile oxides have been investigated. The 1,1-diary1-2-isopropylidene-3-methylenecyclopropanes react with the C,N-diarylnitrones to give a mixture of 2,2-dimethy1-1,6-diary1-3-(diarylmethylene)piperidin-4-ones and 5-methyl-1...

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Published inTetrahedron letters Vol. 53; no. 27; pp. 3411 - 3415
Main Authors Stepakov, Alexander V., Larina, Anna G., Boitsov, Vitaly M., Molchanov, Alexander P., Gurzhiy, Vladislav V., Starova, Galina L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 04.07.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLIC NITRONES
ACID
BUILDING-BLOCKS
ISOXAZOLINE-5-SPIRO DERIVATIVES
2-lsopropylidene-3-methylenecyclopropanes
THERMAL REARRANGEMENT
Nitrones
3-Methylenepiperidin-4-ones
ISOXAZOLIDINES
Nitrile oxides
cycloaddition
ETHYLENE
2,3-Dihydro-3-methylenepyridin-4(1H)-ones,1,3-dipolar
NITRONE CYCLOADDITIONS
PRECURSORS
BETA-LACTAMS
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Summary:The reactions of unactivated bis(methylene)cyclopropanes with nitrones and nitrile oxides have been investigated. The 1,1-diary1-2-isopropylidene-3-methylenecyclopropanes react with the C,N-diarylnitrones to give a mixture of 2,2-dimethy1-1,6-diary1-3-(diarylmethylene)piperidin-4-ones and 5-methyl-1aryl-1-(arylamino)-4-(diarylmethylene)hex-5-en-3-ones. 2,3-Dihydro-3-methylenepyridin-4(1H)-ones are obtained by reaction of 1,1-diary1-2-isopropylidene-3-methylenecyclopropanes with nitrile oxides. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2012.03.093