Rhodium(iii)-catalyzed annulation of 3-arylquinazolinones with alkynes via double C–H activation: an efficient route for quinolino[2,1-b]quinazolinones

Literature Information

Publication Date 2021-09-27
DOI 10.1039/D1QO01186C
Impact Factor 5.281
Authors

Jian Huang, Wei Chen, Jiazhi Liang, Qin Yang, Zhihong Deng, Zhibin Song, Yiyuan Peng


View Original

Abstract

An effective method for the synthesis of quinolino[2,1-b]quinazolinones has been described. The O-directing Rh(III)-catalyzed C–H activation of 3-arylquinazolinones and alkynes gave the corresponding polyaryl substituted quinolino[2,1-b]quinazolinones in good to excellent yields. The results of competition and isotope-labeling experiments support the proposed double C–H activation mechanism. The synthesized quinolino[2,1-b]quinazolinones exhibit a blue-colored emission and large Stokes shifts (67–123 nm) as well as emit visible fluorescence with good fluorescence quantum yields in the solid state.

Related Literature

Metal-free chemoselective hydrogenation of unsaturated carbon–carbon bonds via cathodic reduction

Yongwei Qin, Jingjun Lu, Zirong Zou, Huanliang Hong, Yamei Li, Yibiao Li, Lu Chen, Jinhui Hu, Yubing Huang

2020-06-04 Research Article

DOI: 10.1039/D0QO00547A

Access to SCN-containing thiazolines via electrochemical regioselective thiocyanothiocyclization of N-allylthioamides

Yan-An Zhang, Zhong Ding, Peng Liu, Wei-Si Guo, Li-Rong Wen, Ming Li

2020-04-09 Research Article

DOI: 10.1039/D0QO00300J

Contents list

Front/Back Matter

DOI: 10.1039/D0QO90037K

Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur

Yong-Chao Gao, Zhuo-Bin Huang, Li Xu, Zhao-Dong Li, Zhi-Sheng Lai

2019-02-01 Paper

DOI: 10.1039/C8OB03191F

A fluorogenic C4N4 probe for azide-based labelling

Hidetoshi Noda, Yasuko Asada, Masakatsu Shibasaki, Naoya Kumagai

2018-12-11 Communication

DOI: 10.1039/C8OB02695E

Metal-free difunctionalization of alkynes to access tetrasubstituted olefins through spontaneous selenosulfonylation of vinylidene ortho-quinone methide (VQM)

Zhili Chen, Hui Mao, Fangli Hu, Dongmei Li, Yu Tan, Fengqing Yang, Wenling Qin

2019-01-07 Paper

DOI: 10.1039/C8OB02967A

An Aspidosperma-type alkaloid dimer from Tabernaemontana bovina as a candidate for the inhibition of microglial activation

Si-Meng Zhao, Mei-Fen Bao, Xiang-Hai Cai

2020-04-27 Research Article

DOI: 10.1039/D0QO00296H

Straight access to highly fluorescent angular indolocarbazoles via merging Au- and Mo-catalysis

Fernando Martínez-Lara, Anisley Suárez, Samuel Suárez-Pantiga, M. José Tapia, Roberto Sanz

2020-06-10 Research Article

DOI: 10.1039/D0QO00405G

Recent developments in palladium-catalyzed C–S bond formation

Jianxiao Li, Shaorong Yang, Wanqing Wu, Huanfeng Jiang

2020-04-22 Review Article

DOI: 10.1039/D0QO00377H

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.