Reactions of 1,1-dicyano-2-bis-(trifluoromethyl)-ethylens with enamines
β Scribed by V.Yu. Tyutin; N.D. Chkanikov; A.F. Kolomietz; A.V. Fokin
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- English
- Weight
- 34 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0022-1139
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β¦ Synopsis
A novel reaction of 1,1-dicyano-2-bis (trifluoromethyl) ethylenes (I) with aryl amines in the presence of carbonyl compounds leading to the trifluoromethyl substituted derivatives of 1,4-dihydropyridine is found and investigated.
J X=CF,,CO,AIk
The cyclization reactions (I) with classic enamines are also studied.
π SIMILAR VOLUMES
The interaction of the title compound (BTF) with unsaturated nucleophiles (ketene dithioacetals, a-substituted vinyl ethers, N-vinylcarboxamides, enols, furans, N-methylpyrrole, N-methylindole) effects substitution of vinylic or aromatic H by -C(CF3)2-CH(CN)2. The highly electrophilic 2,2-bis(trifl
Substitution of benzylic H by the title compound (BTF) gives rise to products with -CH(CF3)2 terminus exclusively; an intermediate benzylic ion pair results from hydride transfer. Instead of ion recombination, proton transfer may be the concluding step generating dehydrogenation products and 2,2-bis