Abstract
Transformations of N-aminooxazolidinones were studied. These transformations occur by different pathways depending on the reaction conditions and the structure of the starting compound. Heating of N-aminooxazolidinones in an acidic medium leads to the ring expansion to form 1,3,4-oxadiazin-2-ones. The treatment of N-benzoylamino-and N-benzylamino-oxazolidinones with polyphosphoric acid (PPA) affords tricyclic structures, viz., phthalazine derivatives. In the reactions with PPA, 5-(2-phenylethyl)-substituted N-aminooxazolidinones and 6-(2-phenylethyl)-substituted oxatetrahydropyridazin-2-ones undergo intramolecular amidoalkylation to form compounds containing the tetrahydronaphthalene fragment.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J. M. Joumier, R. Grainger, Ch. Bruneau, and P. H. Dixneuf, Synlett, 1993, 6, 423.
N. B. Chernysheva, A. A. Bogolyubov, and V. V. Semenov, Khim. Geterotsikl. Soedin., 2003, 1212 [Chem. Heterocycl. Compd., 2003 (Engl. Transl.)].
Y. Gohee, A. Boucherle, and M. Robin, Eur. J. Med. Chem.-Chim. Ther., 1986, 21, 403.
B. Fuchs and M. Rosenblum, J. Am. Chem. Soc., 1968, 90, 1061.
N. B. Chernysheva, A. A. Bogolyubov, and V. V. Semenov, Khim. Geterotsikl. Soedin., 1999, 241 [Chem. Heterocycl. Compd., 1999, 35 (Engl. Transl.)].
I. Yu. Titov, N. B. Chernysheva, Yu. B. Chudinov, A. A. Bogolyubov, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 2006, 548 [Russ. Chem. Bull., Int. Ed., 2006, 55, 569].
Yu. B. Chudinov, S. B. Gashev, N. B. Chernysheva, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 2006, 119 [Russ. Chem. Bull., Int. Ed., 2006, 55, 123].
R. J. Tadeschi, A. W. Casey, G. S. Clark, R. W. Huckel, L. M. Kindley, and J. P. Russel, J. Org. Chem., 1963, 28, 1740.
Germ. Pat. 1.098.953; Chem. Abstr., 1962, 56, 245
J. M. Joumier, J. Fournier, Ch. Bruneau, and P. H. Dixneuf, J. Chem. Soc., Perkin Trans. 1, 1991, 3271.
Yu. B. Chudinov, S. B. Gashev, Yu. A. Strelenko, Z. A. Starikova, M. Yu. Antipin, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 2007, 133 [Russ. Chem. Bull., Int. Ed., 2007, 56, No. 1].
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2156–2163, December, 2006.
Rights and permissions
About this article
Cite this article
Chudinov, Y.B., Gashev, S.B. & Semenov, V.V. Synthesis of fused nonaromatic heterocyclic systems based on dioxolanones and hydrazine. Russ Chem Bull 55, 2238–2246 (2006). https://doi.org/10.1007/s11172-006-0578-3
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0578-3