| 刘斌,仝红娟,朱周静,张彦民,郭惠.化学通报,2020,83(10):946-950. |
| 3-仲氨基氧杂环丁烷-3-腈衍生物的合成 |
| Synthesis of 3-Secondary Amine Substituted Oxetane-3-Carbonitrile Derivatives |
| 投稿时间：2020-04-07 修订日期：2020-04-26 |
| DOI： |
| 中文关键词: 氧杂环丁烷 衍生物 三组分反应 合成 |
| 英文关键词:Oxetane Derivative Three-component reaction Synthesis |
| 基金项目:陕西省自然科学基础研究计划（面上）项目（2018JM7046）、陕西省中药绿色制造技术协同创新中心重点培育项目（2019XT-1-05）和陕西国际商贸学院“中药药效物质研究”创新团队项目（SSY18TD01）资助 |
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| 中文摘要: |
| 以仲胺、氧杂环丁-3-酮和三甲基氰硅烷为原料，无水甲醇为溶剂，无需催化剂，一步反应合成目标化合物3-仲氨基氧杂环丁烷-3-腈衍生物（1a~1d），产物结构经1H NMR、13C NMR和ESI-MS表征。并以异吲哚啉、氧杂环丁-3-酮和三甲基氰硅烷的反应为模型反应，考察影响产物1a收率的主要因素，优化反应条件为：物料摩尔比为n（异吲哚啉）：n（氧杂环丁-3-酮）：n（三甲基氰硅烷）=2.0：1：2.5；反应溶剂为无水甲醇，在65℃反应6h，在此反应条件下，化合物1a收率78.3%。化合物1a与苯基溴化镁在四氢呋喃中室温反应5h，可得到2-（3-苯基氧杂环丁烷-3-基）异吲哚啉（4）和[3-（异吲哚啉-2-基）氧杂环丁烷-3-基]（苯基）甲酮（5），收率分别为40.1%和31.5%。 |
| 英文摘要: |
| 3-Secondary amine substituted oxetane-3-carbonitrile derivatives (1a~1d) were synthesized by the reaction of secondary amines with oxetan-3-one and trimethylsilyl cyanide in absolute methanol without catalyst. Their structure was confirmed by 1H NMR, 13C NMR and ESI-MS. The effect of conditions on the yield of product 1a was investigated as model reaction. The optimal conditions on the reaction were as follows: the mole ratio of n (isoindoline):n (oxetan-3-one):n (trimethylsilyl cyanide)=2.0:1:2.5, absolute methanol as solvent, the reaction was at 65℃ for 6h. The product of 1a was obtained in 78.3% yield. The application of the target compound was also investigated. 2-(3-Phenyloxetan-3-yl)isoindoline and (3-(isoindolin-2-yl)oxetan-3-yl)(phenyl)methanone were obtained in a yield of 40.1% and 31.5% by the reaction of 1a and phenylmagnesium bromide in tetrahydrofuran at room temperature for 5h. |
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