Research on imidazo[2,1-α]isoquinoline derivatives. 2. Synthesis and transformations of esters of the imidazo[2,1-α]isoquinoline series
- 47 Downloads
The action of α-halo keto acid esters on 1-aminoisoquinoline was used to synthesize 2- and 3-alkoxycarbonylimidazo[2,1-α]isoquinolines. The 2-ethoxycarbonyl and 2-ethoxycarbonylmethyl derivatives display the typical properties of esters and readily undergo electrophilic substitution (chlorination and bromination) in the 3 position of the system. 3-Alkoxycarbonyl-substituted compounds in which the ester group is attached to the carbon atom with increased electron density do not react with amines; the acid hydrolysis of these compounds is accompanied by elimination of carbon dioxide. Under radical bromination conditions the 3-ethoxycarbonyl-2-methyl derivative is brominated in the methyl group to give monobromoand dibromo-substituted compounds.
KeywordsMethyl Ester Hydrolysis Dioxide Carbon Dioxide
Unable to display preview. Download preview PDF.
- 1.T. A. Kuz'menko, A. M. Simonov, and V. V. Kuz'menko, Khim. Geterotsikl. Soedin., No. 12, 1666 (1976).Google Scholar
- 2.G. Cooper and W. J. Irwin, J. Chem. Soc., Perkin Trans. I, No. 1, 75 (1976).Google Scholar
- 3.J. G. Lombardino, J. Org. Chem., 30, 2403 (1965).Google Scholar
- 4.J. F. Robert, A. Xicluna, and J. J. Panouse, Eur. J. Med. Chem., 10, 59 (1975).Google Scholar
- 5.E. Abignente, F. Arena, P. De Caprariis, and L. Parente, Farm. Ed. Sei., 32, 735 (1977).Google Scholar
- 6.R. M. Elderfield (editor), Heterocyclic Compounds, Vol. 4, Wiley.Google Scholar
- 7.F. Krohnke and W. Zecher, Chem. Ber., 95, 1128 (1962).Google Scholar
- 8.R. Adams and I. J. Pachter, J. Am. Chem. Soc., 76, 1845 (1954).Google Scholar
- 9.H. Reimlinger, F. Billiau, M. A. Peiren, and R. Merenyi, Chem. Ber., 105, 108 (1972).Google Scholar
- 10.V. I. Minkin, B. Ya. Simkin, L. P. Olekhnovich, and M. I. Knyazhanskii, Teor. Éksp. khim., 10, 668 (1974).Google Scholar