Synlett 2020; 31(15): 1497-1500
DOI: 10.1055/s-0040-1706870
letter
© Georg Thieme Verlag Stuttgart · New York

Dearomatization of a 3-Hydroxypyridine Through an Unexpected Oxidative Deformylation Process: An Entry to Azacyclohexadienones

Afef Mabrouki
a   Laboratory of Molecular Organic Chemistry, National Higher Engineering School of Tunis, 5 avenue Taha Hussein, Montfleury, 1089, Tunis, Tunisia
,
Patricia Le Nahenec-Martel
b   Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France   Email: Cyrille.sabot@univ-rouen.fr
,
Abdelkader Kriaa
a   Laboratory of Molecular Organic Chemistry, National Higher Engineering School of Tunis, 5 avenue Taha Hussein, Montfleury, 1089, Tunis, Tunisia
,
Ahmed Hedhli
a   Laboratory of Molecular Organic Chemistry, National Higher Engineering School of Tunis, 5 avenue Taha Hussein, Montfleury, 1089, Tunis, Tunisia
,
Pierre-Yves Renard
b   Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France   Email: Cyrille.sabot@univ-rouen.fr
,
Cyrille Sabot
b   Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014), 76000 Rouen, France   Email: Cyrille.sabot@univ-rouen.fr
› Author Affiliations
This work was funded by the Centre National de la Recherche Scientifique (CNRS), INSA Rouen, Rouen Normandie University, Région Normandie and the Labex SynOrg (ANR-11-LABX-0029).
Further Information

Publication History

Received: 03 June 2020

Accepted after revision: 10 June 2020

Publication Date:
13 July 2020 (online)


Abstract

Phenols are well-known precursors of cyclohexadienones, which have widespread applications in organic synthesis. In contrast, their hydroxypyridine counterparts have not been explored yet. An unprecedented oxidative dearomatization of a 3-hydroxypyridine involving an unexpected deformylation step is reported. The chemical reactivity of the resulting unreported azacyclohexadiene-type compound was also explored.

Supporting Information