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

Chemistry : a European Journal
Thomas P Robinson, Jose M Goicoechea

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.

References

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Aug 25, 2011·Chemical Reviews·Kerry Gilmore, Igor V Alabugin
Aug 6, 2013·Angewandte Chemie·Andrew R Jupp, Jose M Goicoechea
Oct 25, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Dominikus HeiftHansjörg Grützmacher
Dec 10, 2013·Journal of the American Chemical Society·Andrew R Jupp, Jose M Goicoechea
Jan 24, 2014·Angewandte Chemie·Xiaodan ChenHansjörg Grützmacher
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Jul 25, 2014·Chemistry : a European Journal·Dominikus HeiftHansjörg Grützmacher

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Citations

Apr 22, 2017·Chemical Communications : Chem Comm·Jerod M KieserJohn D Protasiewicz
Nov 21, 2017·Angewandte Chemie·Gabriele HierlmeierJose M Goicoechea
Mar 7, 2018·Angewandte Chemie·Yanbo MeiHansjörg Grützmacher
Oct 11, 2017·Physical Chemistry Chemical Physics : PCCP·Sirous YourdkhaniJorge Echeverría
Aug 30, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Sebastian BestgenJose M Goicoechea
May 18, 2018·Angewandte Chemie·Jose M Goicoechea, Hansjörg Grützmacher
Apr 21, 2016·Angewandte Chemie·Alexander Hinz, Jose M Goicoechea
Nov 3, 2017·Chemical Communications : Chem Comm·Robert J GilliardJohn D Protasiewicz
Sep 1, 2016·Chemical Science·Dominikus HeiftHansjörg Grützmacher
Jul 1, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Michal NavrátilPetr Štěpnička
May 3, 2016·European Journal of Inorganic Chemistry·Andrew R JuppJose M Goicoechea
Jan 10, 2018·Angewandte Chemie·Daniel W N WilsonJose M Goicoechea
Sep 19, 2017·Angewandte Chemie·Kevin M SzkopDouglas W Stephan
Dec 16, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Robert J GilliardJohn D Protasiewicz
May 6, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Erica N FariaJose M Goicoechea
Jun 15, 2021·Angewandte Chemie·David A PetroneDouglas W Stephan
Sep 1, 2021·Angewandte Chemie·Grégoire Le CorreHansjörg Grützmacher

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Methods Mentioned

BETA
NMR
X-ray

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