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1,3-Diphenylpropan-1,3-diamines IX. reaction of α-chlorooxime ethers with α-lithiobenzylamines

1,3-Diphenylpropan-1,3-diamine, 9. Mitt. Reaktion von α-Chloroximethern mit α-Lithiobenzylaminen

  • Organische Chemie Und Biochemie
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Summary

The carbanions of the benzylamine derivatives1–4 have been reacted with α-chlorooxime ether5 in order to get precursors of 1,3-diphenylpropane-1,3-diamines. Isonitrile1 afforded the expected result, whereas lithiated benzamide2 underwent oxidative dimerization and transmetallated chlorooxime derivative5. Isoxazolidine3 gave the condensation product21 as a mixture of diastereomers; treatment of imine4 led to the desired amine-oxime15 in low yield.

Zusammenfassung

Die Carbanionen der Benzylaminderivate1–4 wurden mit Chloroximether5 umgesetzt, um Vorstufen von 1,3-Diphenylpropan-1,3-diaminen zu erhalten. Isonitril1 lieferte die erwartete Verbindung, während das lithiierte Benzamid2 oxidativ dimerisiert und das Chloroxim5 ummetallierte. Das Isoxazolidin3 reagierte zu der gewünschten Verbindung21 (Diastereomerengemisch), während das Imin4 in niedriger Ausbeute zum Aminoxim15 führte.

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Authors and Affiliations

  1. Institute of Pharmacy, University of Regensburg, D-93040, Regensburg, Germany

    A. Kaiser & W. Wiegrebe

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  1. A. Kaiser
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  2. W. Wiegrebe
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Dedicated with warm regards to Prof. Dr.J. Knabe, Saarbrücken, Germany, on the occasion of his 75th birthday

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Kaiser, A., Wiegrebe, W. 1,3-Diphenylpropan-1,3-diamines IX. reaction of α-chlorooxime ethers with α-lithiobenzylamines. Monatsh Chem 127, 763–774 (1996). https://doi.org/10.1007/BF00817268

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  • DOI: https://doi.org/10.1007/BF00817268

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