2-Benzopyrylium salts. 44. Formation of 4-acyl-3,4-dihydroisoquinolinium salts from the reaction of 2-benzopyrylium salts with azomethines and the cycloaddition of male-imides to the product of their deprotonation, the 2,3-dihydroisoquinolines
The effect of substituents in the 2-benzopyrylium cation and in the azomethines on the character of their reaction in various solvents has been clarified. It was shown that the 4-acyl-3,4-dihydroisoquinolinium salts resulting after deprotonation form compounds with an ortho-quinonoid structure which then react with maleimides by cycloaddition.
KeywordsOrganic Chemistry Form Compound Deprotonation Form Dihydroisoquinolinium
Unable to display preview. Download preview PDF.
- 1.S. V. Verin and E. V. Kuznetsov, Khim. Geterotsikl. Soedin., No. 2, 169 (1992).Google Scholar
- 2.S. V. Verin, D. E. Tosunyan, P. I. Zakharov, V. K. Shevtsov, and E. V. Kuznetsov, Khim. Geterotsikl. Soedin., No. 9, 1177 (1990).Google Scholar
- 3.E. A. Zvezdina, A. N. Popova, and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., No. 4, 465 (1982).Google Scholar
- 4.I. V. Shcherbakova and E. V. Kuznetsov, Khim. Geterotsikl. Soedin., No. 4, 552 (1982).Google Scholar
- 5.M. Cushman and L. Cheng, J. Org. Chem., 43, 286 (1978).Google Scholar
- 6.G. P. Safaryan, I. V. Shcherbakova, G. N. Dorofeenko, and E. V. Kuznetsov, Khim. Geterotsikl. Soedin., No. 12, 1608 (1981).Google Scholar
- 7.G. N. Dorofeenko, E. A. Zvezdina, and V. V. Derbenev, Zh. Org. Khim., No. 19, 175 (1973).Google Scholar
- 8.S. V. Verin, D. E. Tosunyan, and E. V. Kuznetsov, Khim. Geterotsikl. Soedin., No. 2, 175 (1991).Google Scholar
- 9.R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds [Russian translation], Mir, Moscow (1977), p. 337.Google Scholar
- 10.J. L. Charlton and M. M. Allauddin, Tetrahedron, 43, 2873 (1987).Google Scholar
- 11.V. A. Kovtunenko, E. V. Voitenko, T. T. Kucherenko, A. V. Turov, A. K. Tylin, and F. S. Babichev, Khim. Geterotsikl. Soedin., No. 2, 190 (1990).Google Scholar
- 12.Synthesis of Organic Preparations, No. 2, 164 (1949).Google Scholar