Abstract
1,5-Dinitro-3,7-diazabicyclo[3.3.1]nonane derivatives were synthesized in up to 83%yields by the Mannich reaction of 1,3-dinitropropanes with excess formaldehyde and primary amines. In some cases, for instance, when 2,2-dimethyl-1,3-dinitropropane and benzylamine or monoethanolamine are used, the reaction occurs with low yields or stops at the step of formation of 3,5-dinitropiperidines. The influence of the structure of the starting compounds and reaction conditions on the yields of 1,5-dinitro-3,7-diazabicyclo[3.3.1]nonanes and 3,5-dinitropiperidines was studied.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 405–411, February, 2005.
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Yarmukhamedov, N.N., Baibulatova, N.Z., Dokichev, V.A. et al. One-step synthesis of substituted 3,5-dinitropiperidines and 1,5-dinitro-3,7-diazabicyclo[3.3.1]nonanes from 1,3-dinitropropanes. Russ Chem Bull 54, 414–420 (2005). https://doi.org/10.1007/s11172-005-0265-9
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DOI: https://doi.org/10.1007/s11172-005-0265-9