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Mass-spectrometric study of the cyclization of diazo ketones. 5. Cyclization of phthaloyl dipeptide derivatives of diazomethane

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An analysis of the electron-impact mass spectra of phthaloyl dipeptide derivatives of diazomethane made it possible to conclude that a certain percentage of the [M — N2]+ ions have the 1,3-oxazin-5-one structure, while some of them undergo fragmentation without cyclization. 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 cyclization process is hindered in this case by the introduction of a benzyl substituent in the chain.

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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

Authors
  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 4.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 623–629, May, 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. 5. Cyclization of phthaloyl dipeptide derivatives of diazomethane. Chem Heterocycl Compd 19, 501–507 (1983). https://doi.org/10.1007/BF00514458

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  • DOI: https://doi.org/10.1007/BF00514458

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