Open Access Open Access  Restricted Access Subscription Access

AN UNUSUAL REARRANGEMENT INVOLVING 5-BROMO-1-PHENYLPYRIDONE DURING ITS METHYL CROSS COUPLING WITH TURBO-GRIGNARD REAGENT, LEADING TO A 5-BROMOPYRIDONE-FUSED SEVEN-MEMBERED CARBOCYCLIC RING

Eliezer Falb, Konstantin Ulanenko, Andrey Tor, Michal Afri, Hugo Gottlieb, Alfred Hassner
Cover Image

Abstract


The structure of a cyclohepta[c]pyridin-1-one, a product of an unusual transformation, isolated during a turbo-Grignard reagentpromoted methyl cross coupling to 5-bromo-1-phenyl-2-pyridone, was determined by 1H and 13C NMR, COSY, and high-resolution MS, as well as computer modeling. Its formation suggests a remarkable nucleophilic attack at the α-position to the pyridone carbonyl group. A rational pathway is presented.


Keywords


cyclohepta[c]pyridin-1-one; 3,4-dihydropyridin-2(1H)-one; 3-halo-1-phenylpyridone; turbo-Grignard reagent

Full Text: PDF Supplementary File(s): Supporting information (681KB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv