Synthesis of Spiro and Fused Five Membered N-Heterocycles from Alkylidenephosphoranes

被引：0
作者：
Wafaa M. Abdou
Mounir A. I. Salem
Ashraf A. Sediek
机构：
[1] Department of Pesticide Chemistry,
[2] National Research Centre,undefined
[3] Dokki,undefined
[4] Cairo,undefined
[5] Egypt,undefined
[6] Department of Chemistry,undefined
[7] Faculty of Science,undefined
[8] Ain-Shams University,undefined
[9] Cairo,undefined
[10] Egypt,undefined
来源：
Monatshefte für Chemie / Chemical Monthly | 2003年 / 134卷
关键词：
Keywords.Wittig reaction; α-Iminoketones; Spiro-compounds; Fused N-heterocycles.;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
 Triketoindan-2-oxime reacted readily with ethoxycarbonylmethylene triphenylphosphorane to give mainly the corresponding spiro-pyrrole (38%) along with the fused 1′-hydroxydihydropyrrole (14%), whereas the spiro-dimer (29%) was obtained from the reaction of the oxime with methoxycarbonylmethylenetriphenyl phosphorane in addition to the corresponding 1′-hydroxydihydropyrrole (31%). Conversely, Wittig products, mono-olefin (52%) and diolefin (<7%) along with the reduced substrate (10%), were observed when the oxime was treated with a cyano ylide. The reactions of the oxime with allyl- and vinyl phosphonium salts proceeded under phase-transfer catalysis to afford fused oxazole (46%) and spiro[2]oxazole (17%), while with the latter the fused 1′-hydroxypyrrole (55%) was produced.
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页码：1373 / 1385
页数：12
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