Phosphonic acid analogs of diclofenac: an Arbuzov reaction of trimethylphosphite with an ortho-quinonoid intermediate

The phosphonic acid analog of the NSAID Diclofenac was efficiently synthesized via an Arbuzov reaction between 2-(2,6-dichloroanilino)benzyl alcohol and trimethyl phosphite followed by TMSBr promoted dealkylation. Seven related phosphonic acids were synthesized using the same novel acid-catalyzed Ar...

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Bibliographic Details
Published in:Tetrahedron letters 2000-03, Vol.41 (13), p.2047-2050
Main Authors: Mugrage, Ben, Diefenbacher, Clive, Somers, Joe, Parker, David T, Parker, Tonia
Format: Article
Language:English
Subjects:
Arbuzov reactions
phosphonic acids and derivatives
quinonoid compounds
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Summary:The phosphonic acid analog of the NSAID Diclofenac was efficiently synthesized via an Arbuzov reaction between 2-(2,6-dichloroanilino)benzyl alcohol and trimethyl phosphite followed by TMSBr promoted dealkylation. Seven related phosphonic acids were synthesized using the same novel acid-catalyzed Arbuzov reaction as the key step.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00111-8