铜(I)催化邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯串联双环化反应快速合成5H-苯并咪唑[5,1-b][1,3]噻嗪
收稿日期: 2020-12-02
修回日期: 2021-01-18
网络出版日期: 2021-02-22
基金资助
国家自然科学基金(21762023); 国家自然科学基金(22061021); 江西省自然科学基金(2018BAB203006)
A Rapid Synthesis of 5H-Benzo[d]imidazo[5,1-b][1,3]thiazines via Copper(I)-Catalyzed Cascade Bicyclization ofo-Alkynylphenyl Isothiocyanates with Ethyl (E)-2-(Benzylideneamino)acetates
Received date: 2020-12-02
Revised date: 2021-01-18
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(21762023); National Natural Science Foundation of China(22061021); Natural Science Foundation of Jiangxi Province(2018BAB203006)
以廉价的铜盐作为催化剂, 快速高效地实现了邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯的串联双环化反应, 以中等至良好产率合成了一系列5H-苯并[d]咪唑[5,1-b][1,3]噻嗪类化合物. 该反应操作简单, 利用一步[3+2]环加成继而分子内亲核加成串联机制, 一锅法高效构建了两个新环.
关键词： 铜催化; 串联双环化; 5H-苯并咪唑[5,1-b][1,3]噻嗪
张亚辉 , 吴文锦 , 张可心 , 黎双双 , 郝文燕 . 铜(I)催化邻炔基芳基异硫氰酸酯与(E)-2-(苄基氨基)乙酸酯串联双环化反应快速合成5H-苯并咪唑[5,1-b][1,3]噻嗪[J]. 有机化学, 2021 , 41(5) : 1982 -1990 . DOI: 10.6023/cjoc202012007
A rapid and efficient protocol for copper(I)-catalyzed tandem bicyclization of o-alkynylphenyl isothiocyanates with ethyl (E)-2-(benzylideneamino)acetates has been developed, affording a series of 5H-benzo[d]imidazo[5,1-b][1,3]thia- zines in moderate to good yields. In this transformation, a [3+2] cycloaddition reaction mechanism was involved and two new rings were formed in one pot.
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