- α,β-UNSATURATED THIO COMPOUNDS. XX. -CYCLOADDITION OF 3-AMINO-2-ARYL-1-INDENETHIONES TO NITRILIUM BETAINES AND PHENYL AZIDE
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N,N-Disubstituted 3-amino-2-aryl-1-indenethiones react with the N-oxides of aromatic nitriles or with benzonitrile phenylimine to form 5-spiroindene-substituted 1,4,2-oxathiazoles and 2-spiroindene-substituted 1,3,4-thiadiazolines.With phenyl azide only the transformation of the thiocarbonyl group into a phenylimine group occurs.In the reaction of N-unsubstituted aminoindenethione with benzonitrile N-oxide N,N-diacylation and the parallel transformation of the thione function into ketone function are observed.The reaction of 3-phenylamino-1-indenethione in the iminoenethiol form with benzonitrile N-oxide leads to the product from S-acylation and cycloaddition at the C=N bond with the formation of a 1,4,2-oxadiazoline ring.
- Korchevin, N. A.,Usov, V. A.,Voronkov, M. G.,Borodina, N. M.
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p. 1150 - 1154
(2007/10/02)
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