Abstract
We obtained perhydro-1,2,3-oxathiazine 2,2-dioxides by cyclization of 4-N-benzylamino-4-tetramethylene(phenyl-, methylphenyl-, dimethyl)but-1-enes in conc. H2SO4 at 25°C. When treated with an alcoholic solution of base, the oxathiazines are converted to 2-substituted and spiro-annelated 1-benzyl-4-methylazetidines.
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REFERENCES
K. K. Andersen and M. G. Kocioler, J. Org. Chem., 60, 2003 (1995).
D. Alker, K. J. Doyle, L. M. Harwood, and A. McGregor, Tetrahedron Asymmetry, 1, 877 (1990).
A. V. Varlamov, F. I. Zubkov, A. I. Chernyshev, V. V. Kuznetsov, and A. P. Pal'ma, Khim. Geterotsikl. Soedin., 223 (1999).
L. M. Vargas, W. Rozo, and V. V. Kouznetsov, Heterocycles, 53, 785 (2000).
V. V. Kuznetsov, S. V. Lantsetov, A. E. Aliev, A. V. Varlamov, and N. S. Prostakov, Zh. Org. Khim., 28, 74 (1992).
A. V. Varlamov, V. V. Kouznetsov, F. I. Zubkov, A. I. Chernyshev, G. G. Alexandrov, A. Palma, L. Vargas, and S. Salas, Synthesis, 849 (2001).
V. V. Kuznetsov, A. E. Aliev, and N. S. Prostakov, Khim. Geterotsikl. Soedin., 73 (1994).
L. Y. Vargas and V. Kouznetsov, Heterocycl. Commun., 4, 341 (1998).
B. J. Littler, T. Gallagher, I. K. Boddy, and P. D. Riordan, Synlett, 22 (1997).
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Varlamov, A.V., Sidorenko, N.V., Zubkov, F.I. et al. Substituted and Spiro-annelated Perhydro-1,2,3-oxathiazine 2,2-Dioxides and 1-Benzyl-4-methylazetidines. Chemistry of Heterocyclic Compounds 40, 1097–1105 (2004). https://doi.org/10.1023/B:COHC.0000046704.43034.bd
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DOI: https://doi.org/10.1023/B:COHC.0000046704.43034.bd