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Mass-spectrometric study of the cyclization of diazo ketones. 6. Cyclization of 1-diazo-3-aroylaminopropan-2-ones and 2-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ones

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Abstract

An analysis of the electron-impact mass spectra of 1-diazo-3-aroylaminopropan-2-ones made it possible to conclude that some [M — N2]+ ions have the 1,3-oxazin-5-one structure, some exist in the form of a cyclic intermediate that is produced in the first step of the cyclization process, and some decompose without rearrangements, i.e., they exist in a linear form. The Wolff rearrangement does not occur. Alkyl substituents in the 4 position of the resulting heterocycle hinder cyclization. Under chemical-ionization conditions the [MH — N2]+ ions exist in similar forms. The analysis of the mass spectra in this case is complicated by ion-molecular reactions.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    A. T. Lebedev, P. A. Sharbatyan, A. M. Sipyagin, V. G. Kartsev & V. S. Petrosyan

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  1. A. T. Lebedev
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  2. P. A. Sharbatyan
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  3. A. M. Sipyagin
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  4. V. G. Kartsev
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  5. V. S. Petrosyan
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Additional information

See [1] for communication 5.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1332–1338, October, 1983.

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Lebedev, A.T., Sharbatyan, P.A., Sipyagin, A.M. et al. Mass-spectrometric study of the cyclization of diazo ketones. 6. Cyclization of 1-diazo-3-aroylaminopropan-2-ones and 2-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ones. Chem Heterocycl Compd 19, 1059–1065 (1983). https://doi.org/10.1007/BF00505752

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  • DOI: https://doi.org/10.1007/BF00505752

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