Synthesis of novel piperazine based building blocks: 3,7,9-triazabicyclo[3.3.1]nonane, 3,6,8-triazabicyclo[3.2.2]nonane, 3-oxa-7,9-diazabicyclo[3.3.1]nonane and 3-oxa-6,8-diazabicyclo[3.2.2]nonane |
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Authors: | Laszlo Revesz Ernst Blum Reto Wicki |
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Institution: | Novartis Institutes for BioMedical Research, Global Discovery Chemistry, CH-4002 Basel, Switzerland |
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Abstract: | The preparation of four novel bridged piperazine building blocks is described: 3,7,9-triazabicyclo3.3.1]nonane 1, 3-oxa-7,9-diazabicyclo3.3.1]nonane 2, 3,6,8-triazabicyclo3.2.2]nonane 3 and 3-oxa-6,8-diazabicyclo3.2.2]nonane 4. The scaffold of 1 was synthesized from N,N′-dibromobenzenesulfonamide and ethyl acrylate. Compound 2 may be prepared from identical starting materials or alternatively from α,α′-diglycerol. Compounds 3 and 4 were identified as side products from possible aziridinium intermediates. |
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Keywords: | Bridged piperazines |
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