5-烷氧基-3,4-二卤-2(5H)-呋喃酮与不饱和胺的反应研究

doi:10.6023/cjoc1107142

有机化学 ›› 2012, Vol. 32 ›› Issue (01): 95-103.DOI: 10.6023/cjoc1107142 上一篇下一篇

研究论文

5-烷氧基-3,4-二卤-2(5H)-呋喃酮与不饱和胺的反应研究

陈任宏^a, 傅建花^b, 李国良^b, 谭越河^b, 汪朝阳^b, 袁萍^a

a 广东食品药品职业学院广州 510520;
b 华南师范大学化学与环境学院广州 510006

收稿日期:2011-07-14 修回日期:2011-09-02 发布日期:2011-09-26
通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com
基金资助:
国家自然科学基金(No. 20772035)、广东省高等学校人才引进专项资金(No. 粤财教[2011]431 号)、广东省自然科学基金(Nos. 5300082,S2011010001556)资助项目.

Researches on the Reaction of 5-Alkoxy-3,4-dihalo-2(5H)-furanones with Unsaturated Amines

Chen Renhong^a, Fu Jianhua^b, Li Guoliang^b, Tan Yuehe^b, Wang Zhaoyang^b, Yuan Ping^a

a Guangdong Food and Drug Vocational College, Guangzhou 510520;
b School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received:2011-07-14 Revised:2011-09-02 Published:2011-09-26
Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com
Supported by:
Project supported by National Natural Science Foundation of China (No. 20772035), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (Nos. 5300082, S2011010001556).

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摘要/Abstract

为了深入探索5-烷氧基-3,4-二卤-2(5H)-呋喃酮与胺类试剂发生的反应, 进一步在氟化钾作催化剂和四氢呋喃作溶剂的条件下, 研究了其与系列不饱和胺的反应, 通过旋光度, UV-Vis, IR, ¹H NMR, ¹³C NMR, MS, 元素分析和X 射线单晶衍射等表征方法对产物进行结构表征, 发现大多数情况下发生预期的串联迈克尔加成-消除反应, 得到了16 个新的β-胺基-2(5H)-呋喃酮化合物. 当不饱和胺为空间位阻较大的2,5-二甲基-3-吡咯啉时, 与位阻较大的5-孟氧基-3,4-二卤-2(5H)-呋喃酮反应只是生成异常的2(5H)-呋喃酮开环产物, 而与位阻较小的5-甲氧基-3,4-二卤-2(5H)-呋喃酮反应则既有正常的β-胺基-2(5H)-呋喃酮产物, 也有经开环重排反应的机理得到的异构体产物. 后者表明, 底物的位阻大小也是影响反应的因素, 甚至导致同时存在竞争反应.

关键词: 5-烷氧基-3,4-二卤-2(5H)-呋喃酮, 不饱和胺, 串联迈克尔加成-消除反应, β-胺基-2(5H)-呋喃酮, 开环重排反应, 空间位阻, 竞争反应

In order to further explore the reactions of 5-alkoxy-3,4-dihalo-2(5H)-furanone with amines, the reactions with a series of unsaturated amines were investigated using KF as catalyst and THF as solvent. Sixteen new β-amino-2(5H)-furanone products were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases, and their chemical structures and absolute configurations were confirmed via rotation, UV-Vis, IR, ¹H NMR, ¹³C NMR, MS, elemental analysis and X-ray single crystal diffraction. However, the reaction between 2,5-dimethyl-3-pyrroline and 5-menthoxy-3,4-dihalo- 2(5H)-furanones with larger steric hindrance just yielded unexpected 2(5H)-furanone ring-opening products, while 5-methoxy-3,4-dihalo-2(5H)-furanones with smaller steric hindrance gave both expected β-amino-2(5H)-furanones and unexpected isomers involving the ring-opening rearrangement mechanism. The latter indicated that the steric hindrance of substrates could affect the reactions and even cause competitive reaction.

Key words: 5-alkoxy-3,4-dihalo-2(5H)-furanone, unsaturated amine, tandem Michael addition-elimination reaction, β-amino-2(5H)-furanone, ring-opening rearrangement reaction, steric hindrance, competitive reaction

引用此文

陈任宏, 傅建花, 李国良, 谭越河, 汪朝阳, 袁萍. 5-烷氧基-3,4-二卤-2(5H)-呋喃酮与不饱和胺的反应研究[J]. 有机化学, 2012, 32(01): 95-103.

Chen Renhong, Fu Jianhua, Li Guoliang, Tan Yuehe, Wang Zhaoyang, Yuan Ping . Researches on the Reaction of 5-Alkoxy-3,4-dihalo-2(5H)-furanones with Unsaturated Amines[J]. Chin. J. Org. Chem., 2012, 32(01): 95-103.

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5-烷氧基-3,4-二卤-2(5H)-呋喃酮与不饱和胺的反应研究

Researches on the Reaction of 5-Alkoxy-3,4-dihalo-2(5H)-furanones with Unsaturated Amines

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