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.
Similar content being viewed by others
Literature cited
A. T. Lebedev, P. A. Sharbatyan, A. M. Sipyagin, V. G. Kartsev, and V. S. Petrosyan, Khim. Geterotsikl. Soedin., No. 5, 623 (1983).
V. G. Kartsev and A. M. Sipyagin, Khim. Geterotsikl. Soedin., No. 10, 1324 (1980).
P. A. Sharbatyan, A. T. Lebedev, V. G. Kartsev, and A. M. Sipyagin, Khim. Geterotsikl. Soedin., No. 1, 43 (1981).
P. Kinson and B. M. Trost, Tetrahedron Lett., 14, 1075 (1969).
K. P. Zeller, H. Meier, and E. Mueller, Tetrahedron, 49, 5831 (1972).
K. P. Zeller, Org. Mass Spectrom., 10, 317 (1975).
P. A. Sharbatyan, A. T. Lebedev, A. M. Sipyagin, V. G. Kartsev, and V. S. Petrosyan, Khim. Geterotsikl. Soedin., No. 3, 344 (1982).
R. G. Kostyanovskii, A. V. Prosyanik, A. I. Ermakov, I. A. Zon, Kh. Khafizov, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 119 (1973).
P. B. Terent'ev, Khr. Ivanov, and A. Dobrev, Khim. Geterotsikl. Soedin., No. 12, 1627 (1980).
K. Kägi, Helv. Chim. Acta, 24, 141 (1941).
H. W. Leung and A. G. Harrison, Org. Mass Spectrom., 12, 582 (1977).
A. G. Harrison and P. H. Lin, Can. J. Chem., 53, 1314 (1975).
H. W. Leung and A. G. Harrison, Can. J. Chem., 54, 3439 (1976).
A. T. Lebedev, P. A. Sharbatyan, A. M. Sipyagin, V. G. Kartsev, and V. S. Petrosyan, Khim. Geterotsikl. Soedin., No. 7, 919 (1982).
Author information
Authors and Affiliations
Additional information
See [1] for communication 5.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1332–1338, October, 1983.
Rights and permissions
About this article
Cite this article
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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00505752