Unusual rearrangement of spiro β-lactams to 1,4-diazabicyclo[4,4,0]decanes and 1,4-diazabicyclo[4,3,0]nonanes. Synthesis of conformationally restricted σ-receptor ligands |
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Abstract: | Synthesis of 1,4-diazabicyclo4,4,0]decanes and 1,4-diazabicyclo4,3,0]nonanes was achieved by using 4-formyl spiro β-lactams as easily available starting materials. Furthermore, the application of this protocol to the preparation of conformationally restricted σ-receptor ligands was also performed. Theoretical calculations were carried out on a model reaction, in order to give some understanding of the reaction mechanism. |
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Keywords: | Rearrangement Spiro β-lactams 1 4-Diazabicyclo[4 4 0]decanes 1 4-Diazabicyclo[4 3 0]nonanes Retro-Mannich reactions σ-Receptors |
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