Synthesis of 1‐Aminoisoquinolines and Their Application in a Host‐Guest Doped Strategy To Construct Ultralong Room‐Temperature Phosphorescence Materials for Bioimaging DOI

Lepeng Chen,

Wenzhang Xiong,

Yaogeng Ma

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(5)

Published: Nov. 3, 2022

Organic ultralong room-temperature phosphorescence (RTP) materials have attracted great attention for their wide applications in optoelectronic devices and bioimaging. However, the development of these remains a challenging task, partially due to lack rational molecular design strategies unclear luminescence mechanisms. Herein, we present method facile access structurally diverse substituted 1-aminoisoquinoline derivatives through copper-catalyzed one-pot three-component coupling reaction that provides promising approach rapidly assemble library 1-aminoisoquinolines exploring regularity host-guest doped system. A series RTP with wide-ranging lifetimes from 4.4 299.3 ms were constructed by doping various isoquinolines into benzophenone (BP). Furthermore, 4 r/BP nanoparticles could be used in-vivo imaging signal-to-noise ratio value as high 32, revealing potential isoquinoline framework construction high-performance materials.

Language: Английский

Annulations of Ynamides with 1,2-Benzisothiazoles to Construct 1,4-Benzothiazepines and 3-Aminoisoquinolines DOI
Xiaona Wang, Zhen Zhao,

Jinyue Chen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1522 - 1527

Published: Feb. 13, 2024

Two distinct TMSOTf-catalyzed annulation reactions between ynamides and 1,2-benzisothiazoles have been developed. The direction of the reaction could be easily switched by applying different thermodynamic-controlled conditions. At room temperature, undergo a [5 + 2] with to afford 1,4-benzothiazepines, whereas under heating conditions desulfurizative proceeds well access 3-aminoisoquinolines. These two protocols provide biologically important 1,4-benzothiazepines 3-aminoisoquinolines high efficiency broad substrate scopes mild

Language: Английский

Citations

3

Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent DOI
Jiang Nan, Hanqing Zhang, Lanxin Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones high chemoselectivity. In this discovery, blooms as a multifunctional reagent to participate in cyclization. The potential new finding is further emphasized by assembling the benzothiazole heteroarene via [4 version tolerating bioactive units well.

Language: Английский

Citations

0

Rhodium(iii)-catalyzed oxidative annulation ofN-arylbenzamidines with maleimidesviadual C–H activation DOI

G. Siva Sankaram,

Tanmoy Sahoo, Balasubramanian Sridhar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(8), P. 1719 - 1724

Published: Jan. 1, 2023

An oxidative annulation of N-arylbenzimidamides with maleimides has been developed for the first time using a catalytic amount [Cp*RhCl2]2 complex synthesis diverse range 1H-benzo[4,5]imidazo[2,1-a]pyrrolo[3,4-c]isoquinoline-1,3(2H)-dione derivatives. This method is versatile and atom-economical producing polycyclic benzo[4,5]imidazo[2,1-a]pyrrolo[3,4-c] isoquinoline-1,3(2H)-dione scaffolds in single step.

Language: Английский

Citations

7

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry DOI

Archana Vijayakumar,

M. Manod,

Raveendran Bharath Krishna

et al.

RSC Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 14(12), P. 2509 - 2534

Published: Jan. 1, 2023

This review will be an essential toolbox for medicinal and bioorganic chemists seeking novel multifunctional hybrid bioactive N-heterocycles drug discovery. The work highlights the need relevance of unexplored bioisosterism employing isoquinoline-based small-molecules in design.

Language: Английский

Citations

7

Recent advances of versatile reagents as controllable building blocks in organic synthesis DOI
Shaomin Chen, Luigi Vaccaro, Yanlong Gu

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109152 - 109152

Published: Sept. 27, 2023

Language: Английский

Citations

7

Rh(III)‐Catalyzed Divergent C2‐carboxymethylation of Indoles and C7‐formylmethylation of Indolines with Vinylene Carbonate DOI

Weinan Hu,

Xu Wang,

Xiaoni Yu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(10), P. 2557 - 2561

Published: Sept. 3, 2021

Abstract A Rh‐catalyzed divergent alkylation of indole derivatives with vinyl carbonate was described. Depending on the substrate and solvent, indoles reacted alcohols to give C2 carboxymethylated adducts via a sequential three‐component reaction, while indolines in toluene provide C7 formylmethylated products. The structures product 3 5 were further confirmed by X‐ray analysis. current protocol featured broad scope, tunable reaction conditions, functionalization, good regioselectivity.

Language: Английский

Citations

18

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives DOI Creative Commons
Yi‐Chun Chen,

Ziqi Lu,

Wenfen He

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(7), P. 4804 - 4809

Published: Jan. 1, 2024

The step-economical synthesis of C2, C3-unsubstituted 1-aminoindole derivatives through rhodium-catalyzed annulation hydrazines with vinylene carbonate.

Language: Английский

Citations

2

Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides DOI
Xiaogang Wang, Fei Yuan, Michal Szostak

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(50), P. 10951 - 10957

Published: Dec. 10, 2024

Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly multisubstituted aminoisoquinolines, class heterocycles that play privileged role in organic synthesis pharmaceutical development. This new catalytic process exhibits programmability, including directed C–H acetylation, nucleophilic cyclization, alcoholysis. Remarkably, various 2-arylquinazolinones could be employed excellent yields broad functional group tolerance. heterocycle-to-heterocycle protocol is compatible green chemistry using an EtOH solvent releasing H2O dimethyl sulfoxide as byproducts.

Language: Английский

Citations

2

Rhodium‐Catalyzed C−H Activation/Annulation of N‐Aryl‐pyrazolidinones with Vinylene Carbonate DOI
Gao Huang, Jin‐Tao Yu, Changduo Pan

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(19)

Published: April 21, 2022

Abstract A rhodium‐catalyzed C−H activation/annulation of N ‐aryl‐pyrazolidinones with vinylene carbonate was developed. The utilization as the acetylene surrogate furnished successful construction non‐substituted 5,6‐pyrazolo[1,2‐ a ]cinnoline derivatives, which are difficult to synthesize through other procedures. In this work, series variously substituted pyrazolo[1,2‐ ]cinnolines were obtained in yields up 98 % broad substrate scope and excellent selectivity. Moreover, external oxidants not required protocol H 2 O CO clean by‐products.

Language: Английский

Citations

11

A substrate-controlled Ru(ii)-catalyzed C–H activation/[5 + 2] annulation cascade and unusual acyl migration to synthesize diverse indoline scaffolds DOI

Miao Zheng,

Jianhui Zhou,

Feifei Fang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 62 - 67

Published: Nov. 8, 2022

A substrate-controlled Ru( ii )-catalyzed C–H activation/[5 + 2] annulation cascade and unusual acyl migration to synthesize diverse indoline scaffolds are reported.

Language: Английский

Citations

10