Synthesis and properties of pyrimido[4,5-a]- and pyrido[4,3-a]carbazole derivatives |
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| Authors: | S. Yu. Kukushkin P. Yu. Ivanov L. M. Alekseeva K. I. Kobrakov V. G. Granik |
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| Affiliation: | (1) State Scientific Center of Antibiotics (SSCA), 3a ul. Nagatinskaya, 117003 Moscow, Russian Federation;(2) A. N. Kosygin Moscow State University of Textile, 1 ul. M. Kaluzhskaya, 119991 Moscow, Russian Federation |
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| Abstract: | Methods for the synthesis of substituted pyrimido [4,5-a]- and pyrido[4,3-a]carbazoles were proposed. Condensation of 2-(dimethylaminomethylene)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one with guanidine and thiourea afforded 2-amino-8-methyl-6,11-dihydro-5H-pyrimido[4,5-a]carbazole and 8-methyl-3,5,6,11-tetrahydro-2H-pyrimido[4,5-a]carbazole-2-thione, respectively. The reaction of cyano(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-ylidene)acetamide with dimethylformamide dimethyl acetal gave N-(dimethylamino-methylene)cyano(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-ylidene)acetamide. Cyclization of the latter yielded 1-cyano-8-methyl-3,5,6,11-tetrahydro-2H-pyrido[4,3-a]carbazol-2-one.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2740–2744, December, 2004. |
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| Keywords: | tetrahydrocarbazol-1-ones pyrimido[4,5-a]carbazoles pyrido[4,3-a]carbazoles 2-substituted pyrimidines acyl enamines guanidine thiourea dimethylformamide dimethyl acetal |
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