Rh(III)-Catalyzed C(7)-H Alkylation of Quinolines in the Synthesis of Angular it-Extended Pyrroloquinolines for Single-Component White-Light Emission

被引：8
作者：
Khot, Nandkishor Prakash [1 ]
Mahato, Paritosh [1 ]
Sajeev, T. K. [2 ]
Mukherjee, Saptarshi [1 ]
Kapur, Manmohan [1 ]
机构：
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, MP, India
[2] Indian Inst Sci Educ & Res Bhopal, Dept Biol Sci, Bhopal 462066, MP, India
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 11期
关键词：
C-H FUNCTIONALIZATION; DIAZO-COMPOUNDS; N-OXIDES; 8-AMINOQUINOLINE; DERIVATIVES; FORM;
D O I：
10.1021/acs.orglett.2c00503
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reported herein is a sustainable approach for a regioselective, Rh(III)-catalyzed C(7)-H alkylation of 8aminoquinolines via metal carbene migratory insertion. This transformation displays a high functional group tolerance and exquisite site selectivity to afford the C-7 alkylated products. These products are derivatized to afford pi-extended angular pyrroloquinolines, one of which (4h) shows white-light emission (WLE) with CIE coordinates (0.26, 0.34). An excellent cell viability and in vivo cellular imaging substantiate the nontoxic nature of these compounds.
引用
收藏
页码：2186 / 2191
页数：6
相关论文
共 37 条
[1]   "Rollover" cyclometalation - early history, recent developments, mechanistic insights and application aspects [J].
Butschke, Burkhard ;
Schwarz, Helmut .
CHEMICAL SCIENCE, 2012, 3 (02) :308-326
[2]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[3]   Amino proton donors in excited-state intramolecular proton-transfer reactions [J].
Chen, Chi-Lin ;
Chen, Yi-Ting ;
Demchenko, Alexander P. ;
Chou, Pi-Tai .
NATURE REVIEWS CHEMISTRY, 2018, 2 (07) :131-143
[4]   Color-Tunable and ESIPT-Inspired Solid Fluorophores Based on Benzothiazole Derivatives: Aggregation-Induced Emission, Strong Solvatochromic Effect, and White Light Emission [J].
Chen, Yahui ;
Fang, Yu ;
Gu, Hao ;
Qiang, Jian ;
Li, Haidong ;
Fan, Jiangli ;
Cao, Jianfang ;
Wang, Fang ;
Lu, Sheng ;
Chen, Xiaoqiang .
ACS APPLIED MATERIALS & INTERFACES, 2020, 12 (49) :55094-55106
[5]   8-Aminoquinoline: A Powerful Directing Group in Metal-Catalyzed Direct Functionalization of C-H Bonds [J].
Corbet, Matthieu ;
De Campo, Floryan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :9896-9898
[6]   Pyrroloquinoline scaffold-based 5-HT6R ligands: Synthesis, quantum chemical and molecular dynamic studies, and influence of nitrogen atom position in the scaffold on affinity [J].
Grychowska, Katarzyna ;
Kurczab, Rafal ;
Sliwa, Pawel ;
Satala, Grzegorz ;
Dubiel, Krzysztof ;
Matloka, Mikolaj ;
Moszczynski-Petkowski, Rafal ;
Pieczykolan, Jerzy ;
Bojarski, Andrzej J. ;
Zajdel, Pawel .
BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (12) :3588-3595
[7]   Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping Stone [J].
Hwang, Heejun ;
Kim, Jinwoo ;
Jeong, Jisu ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (30) :10770-10776
[8]   Powerful Direct C-H Amidation Polymerization Affords Single-Fluorophore-Based White-Light-Emitting Polysulfonamides by Fine-Tuning Hydrogen Bonds [J].
Hwang, Soon-Hyeok ;
Kim, Hongsik ;
Ryu, Hanseul ;
Serdiuk, Illia E. ;
Lee, Dongwhan ;
Choi, Tae-Lim .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (04) :1778-1785
[9]   Iridium-Catalyzed Direct C-H Amidation Producing Multicolor Fluorescent Molecules Emitting Blue-to-Red Light and White Light [J].
Hwang, Soon-Hyeok ;
Choi, Tae-Lim .
ORGANIC LETTERS, 2020, 22 (08) :2935-2940
[10]   A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C-H Activation [J].
Hyster, Todd K. ;
Ruhl, Kyle E. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5364-5367
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