Synthesis of 2,2,3,3-tetracyanocyclopropyl ketones and their reactions with oxygen-centered nucleophiles |
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Authors: | I N Bardasov O V Kayukova Ya S Kayukov O V Ershov O E Nasakin V A Tafeenko |
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Institution: | 1.I.N. Ul’yanov Chuvash State University,Cheboksary,Russia;2.Faculty of Chemistry,Moscow State University,Moscow,Russia |
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Abstract: | A procedure for the synthesis of 2,2,3,3-tetracyanocyclopropyl ketones has been developed on the basis of three-component
Wideqvist reaction of dihydroxymethyl ketones, 2-bromomalononitrile, and malononitrile. The presence of five electron-withdrawing
groups in the resulting cyclopropyl ketones determines high acidity of proton in the cyclopropane ring. Facile deprotonation
by the action of bases promotes opening of the three-membered ring with formation of either 1,1,3,3-tetracyanopropenides or
(in the presence of alcohols or oximes), 2-alkoxy(aminooxy)-5-amino-4-cyanofuran-3(2H)-ylidene]malononitriles. The reaction with acetone oxime was not accompanied by cleavage of the three-membered ring, and
nucleophilic attack was directed at the cyano groups in the trans position with respect to the carbonyl group to give the corresponding (1R*,5S*,6R*)-4-amino-2,2-bis(prop-2-ylideneaminooxy)-3-azabicyclo3.1.0]hex-3-ene-1,5-dicarbonitriles. |
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