Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3652-3659.DOI: 10.6023/cjoc202104046 Previous Articles     Next Articles

ARTICLES

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a, 王玉超a, 刘晋彪a,*(), 邱观音生a,b,*()   

  1. 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 发布日期:2021-06-22
  • 通讯作者: 刘晋彪, 邱观音生
  • 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.

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

Shangfeng Rena, Yuchao Wanga, Jinbiao Liua(), Guanyinsheng Qiua,b()   

  1. 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
  • Received:2021-04-21 Revised:2021-05-20 Published:2021-06-22
  • Contact: Jinbiao Liu, Guanyinsheng Qiu
  • 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.

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