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2021 , Vol. 41 >Issue 9: 3652 - 3659

DOI: https://doi.org/10.6023/cjoc202104046

研究论文

N-羟乙基-N-芳基丙炔酰胺的芳基磺酰化及螺-三环化反应

  • 任尚峰 ,
  • 王玉超 ,
  • 刘晋彪 ,
  • 邱观音生
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  • a 江西理工大学材料冶金化学学部 江西赣州 341000
    b 嘉兴学院生物与化学工程学院 浙江嘉兴 314001

收稿日期: 2021-04-21

  修回日期: 2021-05-20

  网络出版日期: 2021-06-22

基金资助

国家自然科学基金(21772067); 国家自然科学基金(21762018); 国家自然科学基金(21961014); 江西省自然科学基金(20171BAB213008); 江西省自然科学基金(20192BCBL23009); 江西省自然科学基金(20202BABL203005); 江西省青年井冈学者奖励计划资助项目.

收起

Arylsulfonylative spiro-Tricyclization of N-Hydroxylethyl- N-arylpropiolamides

  • Shangfeng Ren ,
  • Yuchao Wang ,
  • Jinbiao Liu ,
  • Guanyinsheng Qiu
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  • a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou, Jiangxi 341000
    b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001
* Corresponding authors. E-mail: ;

Received date: 2021-04-21

  Revised date: 2021-05-20

  Online published: 2021-06-22

Supported by

National Natural Science Foundation of China(21772067); National Natural Science Foundation of China(21762018); National Natural Science Foundation of China(21961014); Natural Science Foundation of Jiangxi Province(20171BAB213008); Natural Science Foundation of Jiangxi Province(20192BCBL23009); Natural Science Foundation of Jiangxi Province(20202BABL203005); Youth Jinggang Scholars Program in Jiangxi Province.

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摘要

报道了一种在四丁基碘化铵(TBAI)和过氧硫酸氢钾复合盐(oxone)存在下, 磺酰自由基诱导N-羟乙基-N-芳基丙炔酰胺的螺-三环化串联反应, 并合成了系列1-芳基-2-对甲苯磺酰基-5,6-二氢苯并[b]吡咯并[2,1-c][1,4]噁嗪-3(7aH)-酮. 螺-三环化串联包括磺酰自由基对炔烃的α-加成、ipso-环化和螺环中间体的邻位俘获.

关键词： 螺-三环化反应; 芳基磺酰化; 自由基; 邻位捕获

本文引用格式

任尚峰 , 王玉超 , 刘晋彪 , 邱观音生 . N-羟乙基-N-芳基丙炔酰胺的芳基磺酰化及螺-三环化反应[J]. 有机化学, 2021 , 41(9) : 3652 -3659 . DOI: 10.6023/cjoc202104046

Abstract

A facile procedure is reported for the synthesis of various 1-aryl-2-tosyl-5,6-dihydrobenzo[b]pyrrolo[2,1-c][1,4]- oxazin-3(7aH)-one via a radical arylsulfonylation-induced ipso-cyclization-ortho-cyclization sequence of N-hydroxylethyl-N- arylpropiolamides in the presence of tetra-n-butylammonium iodide (TBAI) and oxone. The radical cyclization sequence involves a sulfonyl radical α-addition into the alkyne, ipso-cyclization, and ortho-trapping of the spirocyclic intermediate.

Key words： spiro-tricyclization; arylsulfonylation; radical; ortho-capture

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