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Interaction of 5,5-dimethyl-2-phenacylpyrroline-1-oxide — an exocyclicβ-oxonitrone — with nucleophilic reagents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A study has been made of the interaction of 2,5,5-trimethylpyrroline-1-oxide with ethyl formate, ethyl thiobenzoate, and methyl nitrate. It has been shown that the reaction of 5,5-dimethyl-2 phenacylpyrroline-1-oxide with methylmagnesium iodide or phenyllithium proceeds through the nitrone group, while the carbonyl group is preserved, after oxidation, this leads to nitroxyl radicals of the pyrrolidine series. Upon interaction of this same N-oxide with nitrogen-containing binucleophiles, recyclization takes place, forming derivatives of isoxazole and pyrazole.

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References

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Authors
  1. V. A. Reznikov
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  2. L. B. Volodarskii
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Additional information

Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 760–769, June, 1996. Original article submitted January 9, 1996.

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Reznikov, V.A., Volodarskii, L.B. Interaction of 5,5-dimethyl-2-phenacylpyrroline-1-oxide — an exocyclicβ-oxonitrone — with nucleophilic reagents. Chem Heterocycl Compd 32, 652–660 (1996). https://doi.org/10.1007/BF01164863

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  • DOI: https://doi.org/10.1007/BF01164863

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