TY - JOUR
T1 - 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
AU - Falb, Eliezer
AU - Ulanenko, Konstantin
AU - Tor, Andrey
AU - Afri, Michal
AU - Gottlieb, Hugo
AU - Hassner, Alfred
N1 - Publisher Copyright:
© 2017, Springer Science+Business Media, LLC, part of Springer Nature.
PY - 2017/9/1
Y1 - 2017/9/1
N2 - [Figure not available: see fulltext.] 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.
AB - [Figure not available: see fulltext.] 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.
KW - 3,4-dihydropyridin-2(1H)-one
KW - 3-halo-1-phenylpyridone
KW - cyclohepta[c]pyridin-1-one
KW - turbo-Grignard reagent
UR - http://www.scopus.com/inward/record.url?scp=85033459964&partnerID=8YFLogxK
U2 - 10.1007/s10593-017-2159-9
DO - 10.1007/s10593-017-2159-9
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AN - SCOPUS:85033459964
SN - 0009-3122
VL - 53
SP - 979
EP - 984
JO - Chemistry of Heterocyclic Compounds
JF - Chemistry of Heterocyclic Compounds
IS - 9
ER -