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Synthesis of Anionic Phosphorus‐Containing Heterocycles by Intramolecular Cyclizations Involving N ‐Functionalized Phosphinecarboxamides
Author(s) -
Robinson Thomas P.,
Goicoechea Jose M.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500628
Subject(s) - intramolecular force , deprotonation , alkyne , chemistry , nucleophile , phosphide , phosphorus , molecule , combinatorial chemistry , medicinal chemistry , ion , stereochemistry , organic chemistry , catalysis
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.