Synthesis of pyrazole- and thiazole-annulated 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes |
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| Authors: | A V Puchnin M A Bastrakov A M Starosotnikov S V Popkov S A Shevelev |
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| Institution: | 1. D. I. Mendeleev University of Chemical Technology of Russia, 9 pl. Miusskaya, 125047, Moscow, Russian Federation
2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
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| Abstract: | The previously unknown 3-R-1,5-dinitro-3-azabicyclo3.3.1]nonanes fused to the pyrazole or thiazole rings were synthesized by the reductive cyclization of m-dinitroindazoles and benzothiazoles. The method is based on the reduction of carbon-carbon bonds in the benzene ring, which are activated by the meta-nitro groups, with NaBH4 followed by the Mannich reaction with formaldehyde and primary amines. |
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