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5-氧代六氢吲哚嗪-8a(1H)-甲醛的合成
发表时间：2018-07-13 浏览量：1214 下载量：251
| 全部作者： | 蒋小燕，何玲，邓军，李卫东 |
| 作者单位： | 重庆大学药学院；西南交通大学生命科学与工程学院 |
| 摘 要： | 报道了含有吡咯并哌啶酮结构的新型类片呐醇重排反应前体化合物的合成。以2-氧代环戊羧酸乙酯作为起始原料，经过烷基化反应、叠氮化反应及Schmidt重排反应构建了吡咯并哌啶酮二环结构，并探究酯的还原条件。研究结果表明，以二异丁基氢化铝（DIBAL-H）为还原剂，能直接将酯还原成醛，得到重排反应前体化合物，为新型类片呐醇重排反应的研究奠定了基础。所有化合物结构均通过光谱数据表征确定。 |
| 关 键 词： | 有机化学；类片呐醇重排；吡咯并[1,2-a]环庚烷；DIBAL-H还原 |
| Title： | Facile synthesis of 5-oxohexahydroindolizine-8a(1H)-carbaldehyde |
| Author： | JIANG Xiaoyan, HE Ling, DENG Jun, LI Weidong |
| Organization： | School of Pharmaceutical Sciences, Chongqing University; School of Life Science and Engineering, Southwest Jiaotong University |
| Abstract： | We herein reported the synthesis of a novel compound bearing pyrrolo-piperidone skeleton, which was the precursor of pinacol-type rearrangement reaction. Using ethyl 2-oxocyclopentanecarboxylate as the raw material, pyrrolo-piperidone skeleton was synthesized via alkylation reaction, azido reaction and Schmidt rearrangement reaction, and then the reduction condition of ester was explored. The results showed that DIBAL-H was a reducing agent which could directly reduce the ester to aldehyde and the precursor compound of rearrangement reaction was obtained. This research laid the foundation to the study of the new pinacol-type rearrangement reaction. The chemical structures of all compounds were determined and characterized by spectroscopic data. |
| Key words： | organic chemistry; pinacol-type rearrangement; pyrrolo[1,2-a]azepine; DIBAL-H reduction |
| 发表期数： | 2018年7月第13期 |
| 引用格式： | 蒋小燕，何玲，邓军，等. 5-氧代六氢吲哚嗪-8a(1H)-甲醛的合成[J]. 中国科技论文在线精品论文，2018，11（13）：1390-1395. |
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