TY - JOUR
T1 - Oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4- naphthoquinone derivatives
AU - Chen, Hui Li
AU - Lin, Chien Yu
AU - Cheng, Yu Chih
AU - Tsai, An I.
AU - Chuang, Che Ping
PY - 2005/4/18
Y1 - 2005/4/18
N2 - A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced effectively in high selectivity. With ethyl 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, in addition to the expected 6-hydroxynaphthacene-5,12-diones, the novel naphtho[2,3-c]furan-4,9- diones were also formed as the major product.
AB - A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced effectively in high selectivity. With ethyl 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, in addition to the expected 6-hydroxynaphthacene-5,12-diones, the novel naphtho[2,3-c]furan-4,9- diones were also formed as the major product.
UR - http://www.scopus.com/inward/record.url?scp=17744373519&partnerID=8YFLogxK
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U2 - 10.1055/s-2005-861850
DO - 10.1055/s-2005-861850
M3 - Article
AN - SCOPUS:17744373519
SN - 0039-7881
SP - 977
EP - 985
JO - Synthesis
JF - Synthesis
IS - 6
ER -