Über Darstellung und Reaktivität von 2,4-Diazabicyclo[3.3.1]nonan-3-onen |
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Authors: | Winfried Wendelin Wolfgang Kern |
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Institution: | (1) Institut für Pharmazeutische Chemie, Universität Graz, A-8010 Graz, Österreich |
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Abstract: | The 2-cyclohexenones1 a andd resp. react with urea in HCl/EtOH to give 1-hydroxy-4-methyl-7-phenyl- and 1-hydroxy-2,4-diazabicyclo3.3.1]nonane-3-ones3a and3d resp., whereas the 2-cyclohexenones1b andc resp. transformed by urea to 1,7-dimethyl- and 1-methyl-4-ureido-2,4-diazabicyclo3.3.1]nonan-3-ones9b andc resp. In the condensation of isophorone1e with urea a product C13H28N8O4 of indisdinct structure was formed, whereas the bicyclus3e could not be isolated.Reaction ofAcOAc with3a yielded the 5-methyl-3-oxo-7-phenyl-2,4-diazabicyclo3.3.1]non-1-ylacetate (15); on heating of3a with acids decomposition to1a and urea took place. NoWagner-Meerwein-rearrangement was observed. The MS-spectra of3a andd are discussed; NMR- and IR-data are reported.No significant herbicidal, fungicidal or insecticidal activity was found in screening-tests on3a. |
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Keywords: | Cyclohexenones reactions with urea 2 4-Diazabicyclo[3 3 1]nonan-3-ones 2-Pyrimidinones bicyclic Urea |
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