Abstract
A one-step synthesis of azetidin-3-ones by intramolecular cyclization of 1-diazo-3-arenesulfamoylalkan-2-ones was developed. The yield of cyclic product increases to 70% in the presence of an alkyl or benzyl substituent in the hydrocarbon chain of the diazoketone. The structure of N-tosyl-2-ethylazetidin-3-one was studied by x-ray diffraction analysis and it was shown that the four-membered ring has 15‡ inflection.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
L. Dall'Asta and A. Pedrazzoli, Experientia, 26, 1207 (1970).
T. Chen, T. Sanjiki, H. Kato, and M. Ohta, Bull. Chem. Soc. Jpn., 40, 2398 (1967).
S. S. Chatterjea and A. Shoeb, Synthesis, No. 3, 153 (1973).
E. H. Gold, German Patent 1,932,985; Chem. Abstr., 72, 66790 (1970).
Z. Sajadi, M. Kashani, L. J. Loeffler, and I. H. Hall, J. Med. Chem., No. 3, 275 (1980).
A. M. Sipyagin and V. G. Kartsev, Zh. Org. Khim., 22, 401 (1986).
G. Sandris and G. Ourisson, Bull. Soc. Chim. Fr., No. 3, 345 (1958).
A. A. Fomichev, I. A. Zon, I. M. Gella, R. G. Kostyanovskii, V. I. Markov, and A. V. Saprin, in: Problems in Stereochemistry [in Russian], Naukova Dumka, Kiev (1973), p. 106.
R. L. Towns and L. M. Trefonas, J. Am. Chem., Soc., 93, 1761 (1971).
R. Chambers and R. J. Doedens, Acta Crystallogr., B36, 1507 (1980).
G. Albers-Schoberg, B. H. Arison, O. D. Hensens, J. Hirshfield, K. Hoogsteen, E. A. Kaczka, R. E. Rhodes, J. S. Kahan, F. M. Kahan, R. W. Ratcliffe, E. Walton, L. J. Ruswinkle, R. B. Morin, and B. G. Christensen, J. Am. Chem. Soc., 100, 6491 (1978).
Ch. Chatterjee, J. K. Dattagupta, and N. N. Saha, Acta Crystallogr., B37, 1835 (1981).
L. V. Vilkov, A. V. Golubinskii, V. S. Mastryukov, N. I. Sadova, L. S. Khaikin, and I. V. Khargittai, in: Contemporary Problems in Physical Chemistry [in Russian], Moscow State University Press, Moscow (1979), Vol. 11, p. 59.
J. J. Worman and M. Boerger, Proc. North Dakota Acad. Sci., 33, 28 (1979).
V. I. Andrianov, Z. Sh. Safina, and B. L. Tarnopol'skii, “Rentgen-75” Programs, Branch of the Institute of Chemical Physics, Academy of Sciences of the USSR, Chernogolovka (1975).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 468–473, April, 1987.
Rights and permissions
About this article
Cite this article
Aliev, Z.G., Atovmyan, L.O., Sipyagin, A.M. et al. Synthesis of azetidin-3-ones. Structure of N-tosyl-2-ethylazetidin-3-one. Chem Heterocycl Compd 23, 390–395 (1987). https://doi.org/10.1007/BF00546731
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00546731