TY - JOUR
T1 - Manganese(III) acetate mediated oxidative radical cyclizations of α-substituted N-[(E)-stilben-2-yl]acetamides
AU - Lin, Ghien An
AU - Chuang, Che Ping
PY - 2015/1/1
Y1 - 2015/1/1
N2 - A synthetic method of 3-substituted 2-quinolinones from readily available α-substituted N-[(E)-stilben-2-yl]acetamides have been developed. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of N-[(E)-stilben-2-yl]acetamides, undergoes an intramolecular 6-exo-dig cyclization onto the CC bond efficiently and 2-quinolinones was produced. A variety of functional groups, including benzoyl, acetyl, cyano, and ethoxycarbonyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O2 conditions, these N-[(E)-stilben-2-yl]acetamides were also converted into the corresponding 2-quinolinones effectively and a catalytic amount of manganese(II) acetate was used.
AB - A synthetic method of 3-substituted 2-quinolinones from readily available α-substituted N-[(E)-stilben-2-yl]acetamides have been developed. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of N-[(E)-stilben-2-yl]acetamides, undergoes an intramolecular 6-exo-dig cyclization onto the CC bond efficiently and 2-quinolinones was produced. A variety of functional groups, including benzoyl, acetyl, cyano, and ethoxycarbonyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O2 conditions, these N-[(E)-stilben-2-yl]acetamides were also converted into the corresponding 2-quinolinones effectively and a catalytic amount of manganese(II) acetate was used.
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U2 - 10.1016/j.tet.2015.05.043
DO - 10.1016/j.tet.2015.05.043
M3 - Article
AN - SCOPUS:84949143643
VL - 71
SP - 4795
EP - 4800
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 29
ER -