Journal
CHINESE CHEMICAL LETTERS
Volume 33, Issue 1, Pages 276-279Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2021.06.081
Keywords
TBAI-catalyzed; Metal-free; Radical cascade; Cyclization; Nitrogen-containing heterocycles; Fused-indole derivatives
Categories
Funding
- State Key Basic Research Program of the People's Republic of China [2018YFC0310900]
- National Natural Science Foundation of China [21871018, 21801005, 21732001]
- Shenzhen Science and Technology Innovation Committee [KQTD20190929174023858, JCYJ20180504165454447]
- Industry and Information Technology Bureau of Shenzhen Municipality [201806151622209330]
- Guangdong Science and Technology Program [2017B030314002]
- Shenzhen-Hong Kong Institute of Brain Science-Shenzhen Fundamental Research Institutions [2019SHIBS0 0 04]
- National Ten Thousand Talent Program (the Leading Talent Tier)
- Science and Technology Project of Henan Province [202102310328]
- Henan Postdoctoral Foundation
- Postdoctoral Innovation Base of Anyang Institute of Technology
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A metal-free radical cascade reaction was developed for the synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolin-6(5H)-one derivatives using readily available sulfonyl hydrazides and N-substituted 2-aryl indoles. The reaction employed a TBAI-TBHP catalytic system and yielded a broad series of structurally diverse derivatives in moderate to excellent yields. The reaction exhibited mild reaction conditions, operational ease, scalability, and high tolerance towards functional groups.
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. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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