N-(5-Fluoro-2-oxo-2,3-dihydro-4-pyrimidinyl)benzamide
CAS Number:
10357-07-0
Molecular Formula:
C11H8FN3O2
B(C6F5)3-catalyzed stepwise 1,5-hydride migration/cyclization: diastereoselective construction of carbocyclic β-amino acid derivatives
Literature Information
Publication Date
2023-12-11
DOI
10.1039/D3QO01637D
Impact Factor
5.281
Authors
Zhiting Wang, Hongchi Liu, Tianxiao Jiang
View Original
Abstract
Concerted 1,5-hydride migration/cyclization reactions represent an efficient approach for the construction of six-membered cyclic scaffolds. However, their applications are severely restricted by the requirement of strongly electron-withdrawing functional groups, expanding conjugation and branched substituents. Herein, a stepwise 1,5-hydride migration/cyclization reaction enabled by B(C6F5)3 is established, where the above limitations could be overcome. The substrate scope is considerably expanded, and a series of amine-tethered simple aliphatic α,β-unsaturated acid derivatives are well compatible, delivering the corresponding six-membered carbocyclic β-amino acid derivatives with complete diastereoselectivity.
Recommended Journals
Russian Journal of Bioorganic Chemistry
Journal of Saudi Chemical Society
Acta Materialia
Nature Medicine
Chemistry Education Research and Practice
Chemical Communications
Russian Journal of General Chemistry
Organic Process Research & Development
Russian Chemical Bulletin
Russian Journal of Organic Chemistry
Related Literature
Theoretical study of electronically excited radical cations of naphthalene and anthracene as archetypal models for astrophysical observations. Part I. Static aspects‡
S. Ghanta, V. Sivaranjana Reddy, S. Mahapatra
2011-07-12
Paper
DOI: 10.1039/C1CP21083A
Preparation of polymer-supported gold nanoparticles based on resins containing ionic liquid-like fragments: easy control of size and stability
M. Isabel Burguete, Eduardo García-Verdugo, Santiago V. Luis, Julián A. Restrepo
2011-07-27
Paper
DOI: 10.1039/C1CP20970A
Nanoparticle-coated separators for lithium-ion batteries with advanced electrochemical performance
Jason Fang, Antonios Kelarakis, Yueh-Wei Lin, Chi-Yun Kang, Ming-Huan Yang, Cheng-Liang Cheng, Yue Wang, Emmanuel P. Giannelis, Li-Duan Tsai
2011-07-06
Communication
DOI: 10.1039/C1CP22017A
Effects of cross-links, pressure and temperature on the thermal properties and glass transition behaviour of polybutadiene
Bounphanh Tonpheng, Junchun Yu, Ove Andersson
2011-07-21
Paper
DOI: 10.1039/C1CP20785G
Interactions of the N3 dye with the iodide redox shuttle: quantum chemical mechanistic studies of the dye regeneration in the dye-sensitized solar cell
Abu Md Asaduzzaman, Georg Schreckenbach
2011-07-20
Paper
DOI: 10.1039/C1CP21168D
Temperature dependent structured absorption spectra of molecular chlorine
I. A. K. Young, C. Murray, C. M. Blaum, R. A. Cox, R. L. Jones, F. D. Pope
2011-07-26
Paper
DOI: 10.1039/C1CP21337G
Bias-controlled selective excitation of vibrational modes in molecular junctions: a route towards mode-selective chemistry
Roie Volkovich, Rainer Härtle, Michael Thoss, Uri Peskin
2011-07-20
Paper
DOI: 10.1039/C1CP21161G
Testing variations of the GW approximation on strongly correlated transition metal oxides: hematite (α-Fe2O3) as a benchmark
Peilin Liao, Emily A. Carter
2011-07-14
Paper
DOI: 10.1039/C1CP20829B
You might also like
Compound Q&A
How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?
2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...
615-45-22-Methylbenzene-1,4-...
Compound Q&A
Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?
(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...
132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A
What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?
(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...
871826-15-2(6-Chloropyridazin-3...
Compound Q&A
What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?
2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...
77772-72-62-Fluoro-3-methylphe...
Compound Q&A
What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?
When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...
177476-75-43-Methoxy-4-nitroben...
Compound Q&A
What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?
When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...
211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A
What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?
4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...
90347-86-74-Ethynylbenzamide
Compound Q&A
What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?
3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...
186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A
What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?
(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...
500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A
What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?
Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...
102196-18-92-[4-(Hydroxymethyl)...
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
4-(Dimethylaminomethyl)phenylacetic acid hydrochloride
CAS Number:
99985-52-1
Molecular Formula:
C11H16ClNO2
![2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate structure](https://static.chemtradehub.com/structs/127/1279090-25-3-1b84.webp "2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate structure")
2-Methyl-2-propanyl {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-oxetanyl}carbamate
CAS Number:
1279090-25-3
Molecular Formula:
C20H30BNO5
![[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid structure](https://static.chemtradehub.com/structs/509/50918-26-8-4ce8.webp "[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid structure")
[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]acetic acid
CAS Number:
50918-26-8
Molecular Formula:
C5H6N2O2S2
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.