Citation: Shengxian Zhai, Shuxian Qiu, Shuai Yang, Bingyan Hua, Yongsheng Niu, Chuchu Han, Youzhu Yu, Yuchao Li, Hongbin Zhai. Synthesis of arylsulfonyl-substituted indolo[2, 1-a]isoquinolin-6(5H)-one derivatives via a TBAI-catalyzed radical cascade cyclization[J]. Chinese Chemical Letters, ;2022, 33(1): 276-279. doi: 10.1016/j.cclet.2021.06.081 shu

Synthesis of arylsulfonyl-substituted indolo[2, 1-a]isoquinolin-6(5H)-one derivatives via a TBAI-catalyzed radical cascade cyclization

Shengxian Zhai ^{a, 1} ,
Shuxian Qiu ^{b, 1} ,
Shuai Yang ^a ,
Bingyan Hua ^a ,
Yongsheng Niu ^{a, *,} ,
Chuchu Han ^a ,
Youzhu Yu ^a ,
Yuchao Li ^a ,
Hongbin Zhai ^{c, *,}

a.
College of Chemistry & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, China
b.
Department of Chemistry, Guangdong University of Education, Guangzhou 510303, China
c.
State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, Shenzhen Graduate School of Peking University, Shenzhen 518055, China

zhaishx@ayit.edu.cn

zhaihb@pku.edu.cn

Received Date: 17 April 2021
Revised Date: 27 June 2021
Accepted Date: 28 June 2021
Available Online: 5 July 2021

Figures(6)

We have developed a metal-free radical cascade reaction of N-substituted 2-aryl indoles with readily available sulfonyl hydrazides for the rapid construction of arylsulfonyl-substituted indolo[2,1-a]isoquinolin-6(5H)-one derivatives. With the TBAI–TBHP catalytic system, a broad series of structurally diverse indolo[2,1-a]isoquinolin-6(5H)-one derivatives were obtained in moderate to excellent yields. The reaction features mild reaction conditions, operationally easiness, scaled-up feasibility, and high functional-group-tolerance.
- TBAI-catalyzed,
- Metal-free,
- Radical cascade,
- Cyclization,
- Nitrogen-containing heterocycles,
- Fused-indole derivatives
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