cis-4,4,6-trimethylbicyclo[3.1.1]heptan-2-one in the synthesis of nitrogen-containing bicyclic compounds |
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Authors: | S S Koval’skaya N G Kozlov |
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Institution: | (1) Institute of Physical Organic Chemistry, Belarussian Academy of Sciences, 220072 Minsk, Belarus |
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Abstract: | cis-4,4,6-Trimethylbicyclo 3.1.1]heptan-2-one (verbanone) in Mannich condensation with paraformaldehyde and dimethylamine adds
an aminomethyl fragment at the most sterically accessible carbon C3 to form an equatorial isomer. The latter treated with sulfuric acid in acetonitrile affords a mixture of two 2-azalactams,
4-(dimethylantinomethyl)-5,7,7-trimethyl-2-azabicyclo4.1.1]octan-3-one and its deamination product 4-methylene-5,5,7-trimethyl-2-azabicyclo4.1.1]octan-3-one
in 9:1 ratio. Z-isomer of amino oxime prepared by oximation of 3-(dimethylaminomethyl)verbanone under similar conditions affords
a mixture of two 3-azalactams, 4-(dimethylaminomethyl)-5,7,7-trimethyl-3-azabicyclo4.1.1]octan-2-one and its deamination
product in 5:3 ratio. Mannich bases prepared from verbanone and its oxime were converted into the respective iodomethylates.
Deamination of the latter results in a single product, α,\-unsaturated ketone 3-methyleneverbanone. |
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