Abstract
It is shown that mixtures of two isomeric benzolactams, viz., compounds of the benzamide and anilide type, are formed in the intramolecular amidation of arylalkylhydroxamic acids under the influence of polyphosphoric acid (PPA). A general reaction scheme that includes three pathways, viz., direct amidation, Lossen rearrangement of the hydroxamic acids with subsequent cyclization of the isocyanates, and Beckmann rearrangement of the oximes of the cyclic ketones formed in the thermal cleavage of the starting hydroxamic acids in PPA, is proposed on the basis of a study of racemic and optically active arylalkylhydroxamic acids.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
E. R. Blout and D. S. Silverman, J. Am. Chem. Soc., 66, 1442 (1944).
P. Camilleri, R. Ellud, A. I. Kirbu, and T. G. Myjahid, J. Chem. Soc., Perkin Trans. II, 12, 1617 (1979).
F. Mauer, L. van Zütphen, and W. Phillips, Chem. Ber., 60, 858 (1927).
J. Colonge and R. Chambard, Bull. Soc. Chim. Fr., No. 3, 982 (1953).
P. T. Lansbury and N. R. Mancuso, J. Am. Chem. Soc., 88, 1205 (1966).
F. W. Wassmund and S. J. Padejimas, J. Am. Chem. Soc., 89, 7131 (1967).
J. T. Marone, Diss. Abstr. Int., B33, 2532 (1972).
J. Suwinski, Zesz. Nauk PS'l. Chem. Pharm. Bull., 19, 1325 (1971).
T. Kametani and H. Nemoto, Chem. Pharm. Bull., 19, 1325 (1971).
P. B. Terent'ev, L. D. Solov'eva, V. M. Dem'yanovich, O. E. Popova, and V. M. Potapov, Khim. Geterotsikl. Soedin., No. 2, 246 (1979).
V. M. Potapov, V. M. Dem'yanovich, L. D. Solov'eva, and A. P. Terent'ev, Dokl. Akad. Nauk SSSR, 185, 614 (1969).
V. M. Potapov, V. M. Dem'yanovich, O. E. Vendrova, and V. A. Khlebnikov, Dokl. Akad. Nauk SSSR, 285, 624 (1981).
V. M. Potapov, V. M. Dem'yanovich, L. D. Solov'eva, and O. E. Vendrova, Khim. Geterotsikl. Soedin., No. 5, 675 (1981).
V. M. Potapov, V. M. Dem'yanovich, O. E. Vendrova, and V. A. Khlebnikov, Zh. Org. Khim., 18, 1205 (1982).
E. S. Wallis and R. D. Dripps, J. Am. Chem. Soc., 55, 1701 (1933).
Y. Barry, H. B. Kagan, and G. Snatzke, Tetrahedron, 27, 4737 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 655–660, May, 1983.
Rights and permissions
About this article
Cite this article
Potapov, V.M., Dem'yanovich, V.M., Vendrova, O.E. et al. Intramolecular amidation of arylalkylhydroxamic acids. Chem Heterocycl Compd 19, 528–533 (1983). https://doi.org/10.1007/BF00514464
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00514464