TY - JOUR
T1 - Influence of the 2-aryl group on the ipso electrophilic substitution process of 2-arylimidazo[1,2-a]pyridines
AU - Salgado-Zamora, Héctor
AU - Velazquez, Manuel
AU - Cervantes, Humberto
AU - Mejia, Daniel
AU - Campos-Aldrete, M. E.
AU - Jimenez, Rogelio
PY - 2008
Y1 - 2008
N2 - A systematic study of electrophilic substitution reactions of 3-nitroso-2-arylimidazo[1,2-α] pyridine confirmed that the nitroso group may be ipso-substituted by bromine (NBS in DMF) and that bromine in turn may be substituted by the nitroso group. Electronic influence of the aryl sustituent at the Imidazopyridine 2-position during the ipso-electrophilic process was experimentally assessed and confirmed by molecular orbital calculations. An ipso electrophilic substitution of bromine in 3-bromo-2-phenylimidazo[1,2-α]pyridine by a nitro group gave different nitro substituted imidazo[1,2-α]pyridine derivatives depending on the nitric acid concentration.
AB - A systematic study of electrophilic substitution reactions of 3-nitroso-2-arylimidazo[1,2-α] pyridine confirmed that the nitroso group may be ipso-substituted by bromine (NBS in DMF) and that bromine in turn may be substituted by the nitroso group. Electronic influence of the aryl sustituent at the Imidazopyridine 2-position during the ipso-electrophilic process was experimentally assessed and confirmed by molecular orbital calculations. An ipso electrophilic substitution of bromine in 3-bromo-2-phenylimidazo[1,2-α]pyridine by a nitro group gave different nitro substituted imidazo[1,2-α]pyridine derivatives depending on the nitric acid concentration.
UR - http://www.scopus.com/inward/record.url?scp=43749116857&partnerID=8YFLogxK
U2 - 10.1515/HC.2008.14.1-2.27
DO - 10.1515/HC.2008.14.1-2.27
M3 - Artículo
SN - 0793-0283
VL - 14
SP - 27
EP - 32
JO - Heterocyclic Communications
JF - Heterocyclic Communications
IS - 1-2
ER -