764654-37-7Relevant articles and documents
Behaviour of N-pyridylbenzamides versus benzanilides in the ortho-directed lithiation of masked aromatic carboxylic acids
Jozwiak, Andrzej,Brzezinski, Jacek Z.,Plotka, Mieczyslaw W.,Szczesniak, Aleksandra K.,Malinowski, Zbigniew,Epsztajn, Jan
, p. 3254 - 3261 (2007/10/03)
The reaction of N-pyridylbenzamides 1-3 with n-butyllithium or sec-butyllithium has been examined. The perfect selectivity that has been observed until now in the lithiation of anilides, a reaction used for ortho-functionalisation of masked aromatic carboxylic acids, has been broken; our results indicate that the pyridine ring at the position ortho to the directed metallation group is more susceptible to lithiation than the homoaromatic ring itself. This was proved in an intermolecular comparative study of benz-, picolin- and isonicotinanilides 14-16, and N-cumylbenzamide (17). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.