TY - JOUR
T1 - Synihesis of 3-substituied indoles via a modified madeling reaction
AU - Orlemans, E.O.M.
AU - Schreuder, A.H.
AU - Conti, P.G.M.
AU - Verboom, Willem
AU - Reinhoudt, David
PY - 1987
Y1 - 1987
N2 - Anilides 4a-c,e-k, lla-d in which the amide function is benzylated, or silylated and having different electron-withdrawing groups (EWG) at the methyl methyl in the ortho position of the amide function, cyclize under the influence of potassium tert-butoxide to the corresponding indole derivatives 5a-c,e-k and 9a-d, respectively, under these conditions the chloroacetamides 4d,n and 11e are converted into the tetrahydroquinolines 6a,b and 12, respectively. Treatment of chloroacetamide 4m with KOt -Bu gave, in addition to starting material, indole 5m, tetrahydroquinoline 6c and 2(1_H)-quinolinone 7. When 3-indolecarbonitrile 5a is treated with sodium in liquid amnonia debenzylation takes place, while after catalytic hydrogenation with 5% Pd/C the corresponding 2,3-dirnethylindole 8 is formed.
AB - Anilides 4a-c,e-k, lla-d in which the amide function is benzylated, or silylated and having different electron-withdrawing groups (EWG) at the methyl methyl in the ortho position of the amide function, cyclize under the influence of potassium tert-butoxide to the corresponding indole derivatives 5a-c,e-k and 9a-d, respectively, under these conditions the chloroacetamides 4d,n and 11e are converted into the tetrahydroquinolines 6a,b and 12, respectively. Treatment of chloroacetamide 4m with KOt -Bu gave, in addition to starting material, indole 5m, tetrahydroquinoline 6c and 2(1_H)-quinolinone 7. When 3-indolecarbonitrile 5a is treated with sodium in liquid amnonia debenzylation takes place, while after catalytic hydrogenation with 5% Pd/C the corresponding 2,3-dirnethylindole 8 is formed.
KW - IR-69918
U2 - 10.1016/S0040-4020(01)86867-8
DO - 10.1016/S0040-4020(01)86867-8
M3 - Article
VL - 43
SP - 3817
EP - 3826
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 16
ER -