TY - JOUR
T1 - Oxidation of dioxopyrroline with m-chloroperbenzoic acid
T2 - Selective formation of 2,3-dioxo-1,4-oxazine
AU - Sano, Takehiro
AU - Amano, Kazuko
AU - Seki, Masaharu
AU - Hirota, Hiroyuki
AU - Toda, Jun
AU - Kiuchi, Fumiyuki
AU - Tsuda, Yoshisuke
PY - 1994/1/1
Y1 - 1994/1/1
N2 - Treatment of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-diones (1a-1e) and 4-benzoyl-1,5-diphenyl-1H-pyrrole-2,3-dione (1f) with m-chloroperbenzoic acid caused Baeyer-Villiger oxidation to give 2,3-dioxo-1,4-oxazines (2a-2f) in moderate yields, respectively. This conversion of the 1H-pyrrole-2,3-dione into the 2,3-dioxo-1,4-oxazine provides the first synthesis of monocyclic 2,3-dioxo-1,4-oxazine ring system.
AB - Treatment of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-diones (1a-1e) and 4-benzoyl-1,5-diphenyl-1H-pyrrole-2,3-dione (1f) with m-chloroperbenzoic acid caused Baeyer-Villiger oxidation to give 2,3-dioxo-1,4-oxazines (2a-2f) in moderate yields, respectively. This conversion of the 1H-pyrrole-2,3-dione into the 2,3-dioxo-1,4-oxazine provides the first synthesis of monocyclic 2,3-dioxo-1,4-oxazine ring system.
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U2 - 10.3987/COM-93-S46
DO - 10.3987/COM-93-S46
M3 - Article
AN - SCOPUS:0343542353
SN - 0385-5414
VL - 37
SP - 523
EP - 528
JO - Heterocycles
JF - Heterocycles
IS - 1
ER -