Synthesis of anionic phosphorus-containing heterocycles by intramolecular cyclizations involving N-functionalized phosphinecarboxamides

Journal article

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.

Authors: Robinson, T; Goicoechea, J

• Publication status: Published
• Peer review status: Peer reviewed
• Publisher: Wiley
• Journal: Chemistry - A European Journal
• Volume: 21
• Issue: 15
• Pages: 5727-5731
• Publication date: 2015-03-03
• DOI: 10.1002/chem.201500628
• EISSN: 1521-3765
• ISSN: 0947-6539
• Language: English
• Keywords: phosphides; 2-phosphaethynolate anion; heterocycles; propargyl-phosphines; phosphorus