Synthesis of Indazolo[2,1-a]Cinnolines via Rhodium (III)-Catalyzed C-H activation/annulation under mild conditions

doi:10.1016/j.tet.2019.06.021

	Synthesis of Indazolo[2,1-a]Cinnolines via Rhodium (III)-Catalyzed C-H activation/annulation under mild conditions
	Hou, Wei 1; Xiong, Huan2 ; Bai, Ruisong 1; Xiao, Zaozao 3; Su, Lin 1; Ruan, Bengfang Helen 1; Xu, Hongtao2
	2019-07-26
发表期刊	TETRAHEDRON
ISSN	0040-4020
卷号	75 期号:30 页码:4005-4009
发表状态	已发表
DOI	10.1016/j.tet.2019.06.021
摘要	A simple, robust and efficient Rh(III)-catalyzed synthesis of novel 12H-indazolo[2,1-a]cinnolin-12-ones has been developed via tandem C-H activation/annulation of 2-phenylindazolones with diazo compounds by using less developed secondary amine as an intrinsic directing group. Notably, a series of nondiscriminating conditions were obtained with excellent test yield. Also, this reaction is highly regioselective with broad substrate scope and both electron-donating and electron-withdrawing groups gave satisfactory yield under very mild conditions (room temperature to 40 degrees C). It is scalable, compatible with air and H2O, and the only by-products are N-2 and H2O. Moreover, the synthesized products represent a new class of fluorophores and their initial spectroscopic characterization has been conducted. (C) 2019 Elsevier Ltd. All rights reserved.
关键词	Rhodium catalysis Strong directing group C-H/N-H functionalization Indazolo[2,1-a]Cinnolines Fluorophores
收录类别	SCI ; SCIE ; IC ; CCR
语种	英语
资助项目	Natural Science Foundation of Zhejiang province/Youth foundation Project, China[LQ19B060005]
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000475998700008
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS关键词	LARGE STOKES-SHIFT ; DIAZO-COMPOUNDS ; RH(III)-CATALYZED SYNTHESIS ; CATALYZED CYCLIZATION ; N-OXIDES ; FUNCTIONALIZATION ; ACTIVATION ; CINNOLINES ; DERIVATIVES ; ANNULATION
原始文献类型	Article
引用统计
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/61072
专题	免疫化学研究所_特聘教授组_功能筛选实验室免疫化学研究所_特聘教授组_抗体设计学实验室
通讯作者	Ruan, Bengfang Helen; Xu, Hongtao
作者单位	1.Zhejiang Univ Technol, Inst Drug Dev & Chem Biol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China 2.ShanghaiTech Univ, SIAIS, Shanghai 201210, Peoples R China 3.Tianjin Univ Sci & Technol, Coll Chem Engn & Mat Sci, Tianjin 300457, Peoples R China
通讯作者单位	上海科技大学
推荐引用方式 GB/T 7714	Hou, Wei,Xiong, Huan,Bai, Ruisong,et al. Synthesis of Indazolo[2,1-a]Cinnolines via Rhodium (III)-Catalyzed C-H activation/annulation under mild conditions[J]. TETRAHEDRON,2019,75(30):4005-4009.
APA	Hou, Wei.,Xiong, Huan.,Bai, Ruisong.,Xiao, Zaozao.,Su, Lin.,...&Xu, Hongtao.(2019).Synthesis of Indazolo[2,1-a]Cinnolines via Rhodium (III)-Catalyzed C-H activation/annulation under mild conditions.TETRAHEDRON,75(30),4005-4009.
MLA	Hou, Wei,et al."Synthesis of Indazolo[2,1-a]Cinnolines via Rhodium (III)-Catalyzed C-H activation/annulation under mild conditions".TETRAHEDRON 75.30(2019):4005-4009.