Abstract
Thermal decarboxylation of 3-p-toluoyl-1,2-dihydro-4H-pyrrolo[5,1-c][1,4]benzoxazine-1, 2,4-trione resulted in 2-oxo-2H-1,4-benzoxazin-3-yl(p-toluoyl)ketene; the latter under-goes [4+2]-cycloaddition withp-bromobenzaldehyde to form 1-p-bromophenyl-4-p-toluoyl-1, 3-dihydro-5H-[1,3]oxazino[4,3-c][1,4] benzoxazine-3,5-dione. The crystal and molecular structure of the latter has been studied by X-ray analysis.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Yu. S. Andreichikov, L. F. Gein, and G. D. Plahina,Zh. Org. Khim., 1980,16, 2336 [J. Org. Chem., 1980,16 (Engl. Transl.)].
M. Sato, K. Sekiguchi, H. Ogasawara, and C. Kaneko,Synthesis, 1985, 224.
R. Smalley, H. Suschitzky, and E. Tanner,Tetrahedron Lett., 1966, 3465.
H. Crabtree, R. Smalley, and H. Suschitzky,J. Chem. Soc., 1968 (C), 2730.
A. N. Maslivets, O. P. Krasnykh, L. I. Smirnova, and Yu. S. Andreichikov,Zh. Org. Khim., 1989,25, 1045 [J. Org. Chem., 1989,25 (Engl. Transl.)].
L. G. Aksel'vrud, Yu. N. Grin', P. Yu. Zavalii,et al., Paket Programm dlya stryktumogo analiza [Program Package for Structural Analysis], L'vov State University, L'vov, 1990 (in Russian).
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1633–1636, September, 1993.
Rights and permissions
About this article
Cite this article
Aliev, Z.G., Maslivets, A.N., Krasnykh, O.P. et al. The [4+2]-cycloaddition of ketene containing both acyl and imidoyl groups to aldehyde: Synthesis, crystal and molecular structure of 1-p-bromophenyl-4-p-toluoyl-1, 3-dihydro-5H-[1,3]oxazino[4,3-c][1,4]benzoxazine-3,5-dione. Russ Chem Bull 42, 1569–1572 (1993). https://doi.org/10.1007/BF00699197
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00699197