The chemistry of bicyclic bisureas. 4. Reduction of bicyclic bisureas and their O-alkyl derivatives
- 22 Downloads
When LiAlH4, is allowed to react with unsubstituted, di-, and tetra-N-alkylated bicyclic bisureas (BBU) of the octane and nonane series, reduction takes place only in the case of tetra-N-alkyl BBU, reduction of one or both carbonyl groups taking place according to the structure of the BBU.
Reaction of non-N-alkylated O-alkyl BBU with nucleophilic reagents results in deprotonation with the formation of bicyclic isoureas.
KeywordsCarbonyl Carbonyl Group Octane Nonane LiAlH4
Unable to display preview. Download preview PDF.
- 1.L. I. Suvorova, L. V. Epishina, O. V. Lebedev, L. I. Khmel'nitskii, and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim., 2282 (1979).Google Scholar
- 2.V. M. Michovich and M. L. Mikhailovich, Lithium Aluminohydride and Its Use in Organic Chemistry [Russian translation], IL (1957).Google Scholar
- 3.S. F. Nelsen and P. J. Hintz, J. Am. Chem. Soc.,94, 7114 (1972).Google Scholar
- 4.R. Borch, Tetrahedron Lett., 61 (1968).Google Scholar
- 5.J. Nematollahi and R. Ketcham, J. Org. Chem.,28, 2378 (1963).Google Scholar
- 6.A. Woerner, O. Grabowsky, H. Scheuermann, W. Trimborn, and A. Vlachos, Ger. Pat. No. 920 965, 6.12.54; Chem. Abstr.,52, 137 859 (1958).Google Scholar
- 7.L. I. Suvorova, V. A. Eres'ko, L. V. Epishina, O. V. Lebedev, L. I. Khmel'nitskii, S. S. Novikov, M. V. Povstyanoi, V. D. Krylov, G. V. Korotkova, L. V. Lapshina, and A. F. Kulik, Izv. Akad. Nauk SSSR, Ser. Khim., 1306 (1979).Google Scholar