Regioselective decarboxylative cross-coupling of carboxy isoquinoline N-oxides.
A straightforward method for direct decarboxylative arylation of 1- and 3-carboxy isoquinaldic acid N-oxides with aryl iodides is reported. The reaction proceeded selectively at the carboxy function site to exclusively give the corresponding C-1 or C-3 arylated product. This methodology tolerates various aryl iodides substituted by electronically different groups. Combined with subsequent Reissert-Henze chlorination and SNAr amination, the decarboxylative arylation provides an efficient access to 1,3-functionalized isoquinoline-based antitumor agent.
Normandie University, COBRA, UMR 6014 et FR 3038, University Rouen, INSA Rouen, CNRS, IRCOF, 1 rue Tesnière, Mont-Saint-Aignan 76821 Cedex, France.
Jean-Baptiste E Y
JB
Rouchet
Normandie University, COBRA, UMR 6014 et FR 3038, University Rouen, INSA Rouen, CNRS, IRCOF, 1 rue Tesnière, Mont-Saint-Aignan 76821 Cedex, France.
Cédric
C
Schneider
Normandie University, COBRA, UMR 6014 et FR 3038, University Rouen, INSA Rouen, CNRS, IRCOF, 1 rue Tesnière, Mont-Saint-Aignan 76821 Cedex, France.
Corinne
C
Fruit
Normandie University, COBRA, UMR 6014 et FR 3038, University Rouen, INSA Rouen, CNRS, IRCOF, 1 rue Tesnière, Mont-Saint-Aignan 76821 Cedex, France.
Christophe
C
Hoarau
D003497:Cyclic N-Oxides / Q000737:chemistry*; D054879:Halogenation; D007454:Iodides / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D003497:Cyclic N-Oxides; D007454:Iodides; D007546:Isoquinolines; C039109:isoquinoline