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94. Substitution and Ring Closure Reactions of Pyrido[3,2,1-jk]carbazol-6-ones
H. V. Dang, B. Knobloch, N. S. Habib, Th. Kappe and W. Stadlbauer, in Proceedings of ECSOC-8, The Eighth International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ecsoc-8.htm, November 1-30, 2004; J. A. Seijas, M. P. Vázquez-Tato (Eds). CD-ROM edition, ISBN 3-906980-15-4; MDPI, Basel, Switzerland, 2004 .

Abstract:
4-Hydroxy-pyrido[3,2,1-jk]carbazol-6-ones (3) which contain two biologically interesting structures, the indole and the 4-hydroxypyridone moiety, are obtained easily by cyclocondensation of carbazoles 1 (R' = H, OH) and monosubstituted malonates 2 . Nucleophilic substitution of the hydroxy group resulted in a number of reactive products such as 4-amino, 4-halogeno, 4-tosyloxy, 4-cyano or 4-azido compounds 4, which could be cyclized e.g. to indolo derivatives 5 or quinolino derivatives 6. Electrophilic substitution took place at the enolized CH-acidic 1,3-dicarbonyl function of 3 to give 5,5-disubstituted pyrido[3,2,1-jk]carbazole-4,6-diones 7 with alkyl, aryl, amino, azido, halogeno, hydroxy or nitro substituents in position 5. The oxo function in position 4 could be exchanged against a carbon function such as alkyl or alkylidene substituents (e.g. 6-oxo-pyrido[3,2,1-jk]carbazol-4-ylideneacetate 8).


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