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Synthesis of β-Enamino Sulfoxides via Cine-Substitution of 1-Chlorovinyl p-Tolyl Sulfoxides with Lithium Amides
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DOI：10.1002/adsc.70584.png)
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Abstract
En 中文
The cine-substitution of 2-aryl-1-chlorovinyl p-tolyl sulfoxides with lithium amides of azoles and anilines and sodium amides of imidazole, carboxamide, and aliphatic amine occurs to yield β-enamino sulfoxides with high efficiency. β-Elimination–addition is a plausible mechanism for cine-substitution. β-Enamino sulfoxides are desulfinylated via the sulfoxide/magnesium exchange reaction with isopropylmagnesium chloride and the protonation of the resulting (2-aminovinyl)magnesium chlorides. N-(α-Styryl)indole is prepared from indole and 1-chloro-2-phenylvinyl p-tolyl sulfoxide through a one-pot procedure involving cine-substitution and desulfinylation.
Keywords:
β-enamino sulfoxides
anilines
azoles
cine-substitution
desulfinylation
N-vinylation
Journal
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IF:
4
Papers:
424
Citations:
0