Synthesis of Anionic Phosphorus‐Containing Heterocycles by Intramolecular Cyclizations Involving N‐Functionalized Phosphinecarboxamides |
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Authors: | Dr Thomas P Robinson Prof Dr Jose M Goicoechea |
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Institution: | Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK) |
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Abstract: | We report that the 2‐phosphaethynolate anion (PCO?) reacts with propargylamines in the presence of a proton source to afford novel N‐derivatized phosphinecarboxamides bearing alkyne functionalities. Deprotonation of these species gives rise to novel five‐ and six‐membered anionic heterocycles resulting from intramolecular nucleophilic attack of the resulting phosphide at the alkyne functionality (via 5‐exo‐dig or 6‐endo‐dig cyclizations, respectively). The nature of the substituents on the phosphinecarboxamide can be used to influence the outcome of these reactions. This strategy represents a unique approach to phosphorus‐containing heterocylic systems that are closely related to known organic molecules with interesting bio‐active properties. |
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Keywords: | 2‐phosphaethynolate anion heterocycles phosphides phosphorus propargyl‐phosphines |
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