Rh(iii)-Catalyzed tandem C(sp2)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates
Literature Information
Publication Date
2021-10-08
DOI
10.1039/D1QO01129D
Impact Factor
5.281
Authors
Hui Xie, Jin-Yi Liang, Zhuo-Jun Huang, Bing Shu, Yi-Chuan Zheng, Yan-Zhi Liu, Shao-Yong Chen, Xu-Ge Liu, Shang-Shi Zhang
View Original
Abstract
A Rh(III)-catalyzed tandem C(sp2)–H allylation/N-alkylation annulation reaction of arene amides employing 5-methylene-1,3-dioxan-2-one as an efficient allyl source has been disclosed for the first time, affording an unprecedented opportunity for the synthesis of 3,4-dihydropyrimido[1,6-a]indol-1(2H)-ones in moderate to excellent yields. Meanwhile, Rh(III)-catalyzed C(sp2)–H allylation products can also be obtained under altered reaction conditions. These practical and scalable divergent synthesis protocols proceeded smoothly under mild reaction conditions. Broad substrate scope, good functional group compatibility and total 32 examples were observed. Moreover, the preliminary mechanism studies show that the rhodium catalyst plays a dual role in the C–H activation and N-alkylation annulation process.
Recommended Journals
Related Literature
Structure and properties of biobased polyamide 36,9/cellulose nanocomposites
Biqiong Chen
2023-10-20
Paper
DOI: 10.1039/D3SU00302G
Nitrogen-doped carbon quantum dots from biomass as a FRET-based sensing platform for the selective detection of H2O2 and aspartic acid
K. Sandeep Raju, Gouri Sankar Das, Kumud Malika Tripathi
2023-11-13
Paper
DOI: 10.1039/D3SU00343D
The critical role of H2 reduction roasting for enhancing the recycling of spent Li-ion battery cathodes in the subsequent neutral water electrolysis
Jiayin Zhou, Jihong Ni, Xiaofei Guan
2023-09-26
Paper
DOI: 10.1039/D3SU00201B
Bio-based polycarbonates: progress and prospects
Mi Feng, Ming Jiang
2023-11-14
Tutorial Review
DOI: 10.1039/D3SU00248A
Moringa pod derived antioxidant dietary fibre as a quality enhancer in goat meat nuggets
Annada Das, S. Biswas, P. K. Nanda, Niloy Chatterjee, Srija Pal, Pubali Dhar, Arun K. Verma, Dipanwita Bhattacharya, Rojison Koshy, Arun K. Das
2024-01-03
Paper
DOI: 10.1039/D3FB00177F
Recent advances in semiconductor heterojunctions: a detailed review of the fundamentals of photocatalysis, charge transfer mechanism and materials
Aniket Balapure, Jayati Ray Dutta, Ramakrishnan Ganesan
2023-09-27
Review Article
DOI: 10.1039/D3LF00126A
Fortification of vegetable fat with natural antioxidants recovered by bergamot pomace for use as an ingredient for the production of biscuits
Amalia Piscopo, Simone Santacaterina, Elisa Imeneo, Alessandra De Bruno, Marco Poiana
2023-10-13
Paper
DOI: 10.1039/D3FB00125C
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
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
![N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure](https://static.chemtradehub.com/structs/238/2387704-62-1-25f4.webp "N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine structure")
N-[(5,6-Dichloro-1H-benzimidazol-2-yl)methyl]-9-(1-methyl-1H-pyrazol-4-yl)-2-(4-morpholinyl)-9H-purin-6-amine
CAS Number:
2387704-62-1
Molecular Formula:
C21H20Cl2N10O
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.