Abstract
Ethyl oxaloacetate reacts with a mixture of an aromatic aldehyde and an arylamine to give 1,5-diaryl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones, which react with diphenyldiazomethane to give the O-alkylation products. On heating, the latter undergo suprafacial [1,3]-sigmatropic rearrangement to 1,5-diaryl-4-diphenylmethyl-4-ethoxycarbonyltetrahydropyrrole-2,3-diones. The effects of the type of migrating group on the rearrangement are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
V. V. Zalesov, N. A. Pulina, and Yu. S. Andreichikov,Zh. Org. Khim. (1989) (in press).
Yu. S. Andreichikov, V. L. Gein, and I. N. Anikina,Khim. Geterotsikl. Soedin., No. 5, 625 (1987).
Yu. S. Andreichikov, V. L. Gein, and I. N. Anikina,Khim. Geterotsikl. Soedin., No. 10, 1428 (1985).
I. J. Simon and A. Conduche,Ann. Chim. 12, 5 (1907).
R. Schiff and C. Bertini,Ber. Chem. Ges. 30, 601 (1897)
J. R. Merchant and V. Srinavasan,Rec. Trav. Chim. 81, 144 (1962).
T. Gilchrist and R. Storr,Organic Reactions and Orbital Symmetry [Russian translation], Mir, Moscow (1976), p. 279.
I. E. Baldwin and J. E. Brown,J. Am. Chem. Soc. 91, 3647 (1969).
A. S. Dneprovskii and T. I. Temnikova,The Theoretical Foundations of Organic Chemistry [in Russian], Khimiya, Leningrad (1979).
Author information
Authors and Affiliations
Additional information
For Communication 14, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 753–757, June, 1990.
Rights and permissions
About this article
Cite this article
Andreichikov, Y.S., Gein, V.L. & Shumilovskikh, E.V. Five-membered 2,3-dioxoheterocycles 15. Synthesis and [1,3]-sigmatropic rearrangement of 1,5-diaryl-3-diphenylmethoxy-4-ethoxycarbonyl-2,5-dihydropyrrol-2-ones. Chem Heterocycl Compd 26, 627–630 (1990). https://doi.org/10.1007/BF00756412
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00756412