TY - JOUR
T1 - Pd-Catalyzed Amidation of 2-Chloro- and 2,7-Dichloro-1,8-naphthyridines
AU - Ligthart, G.B.W.L.
AU - Ohkawa, H.
AU - Sijbesma, R.P.
AU - Meijer, E.W.
PY - 2006
Y1 - 2006
N2 - The catalytic amidation between 2-chloro- and 2,7-dichloro-1,8-naphthyridines and primary amides bearing functional groups is reported. When Pd(OAc)2, xantphos, and K2CO3 are used, it is possible to obtain sym. as well as nonsym. 2,7-diamido-1,8-naphthyridines in 50-90% yield with good functional-group tolerance. Monoamidation of 2,7-dichloro-1,8-naphthyridine using 0.9 equiv of the amide proceeded with good selectivity compared to the formation of the diamide, but as a result of the difficult isolation of the product, isolated yields were poor to moderate (22-42%).
AB - The catalytic amidation between 2-chloro- and 2,7-dichloro-1,8-naphthyridines and primary amides bearing functional groups is reported. When Pd(OAc)2, xantphos, and K2CO3 are used, it is possible to obtain sym. as well as nonsym. 2,7-diamido-1,8-naphthyridines in 50-90% yield with good functional-group tolerance. Monoamidation of 2,7-dichloro-1,8-naphthyridine using 0.9 equiv of the amide proceeded with good selectivity compared to the formation of the diamide, but as a result of the difficult isolation of the product, isolated yields were poor to moderate (22-42%).
U2 - 10.1021/jo051864b
DO - 10.1021/jo051864b
M3 - Article
C2 - 16388663
SN - 0022-3263
VL - 71
SP - 375
EP - 378
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -