![1-oxaspiro[4.4]nonan-6-one structure](https://static.chemtradehub.com/structs/134/134179-01-4-e051.webp "1-oxaspiro[4.4]nonan-6-one structure")
From α-keto acids to nitrile oxides enabled by copper nitrate: a facile access to fused isoxazolines
Literature Information
Publication Date
2021-12-10
DOI
10.1039/D1QO01574E
Impact Factor
5.281
Authors
Yuping Zhu, Tianqi Liu, Bingxin Liu, Houguang Shi, Qitao Tan
View Original
Abstract
α-Keto acids were unprecedentedly employed as novel precursors of nitrile oxides on treatment with copper nitrate, which reacted with maleimides via [3 + 2] dipolar cycloaddition leading to pharmacologically interesting fused isoxazolines. This approach offers a unique strategy and complementary method for the convenient generation of alkyl substituted nitrile oxides, compared with previously reported copper nitrate-mediated alkenes or alkynes transformations. Different from the well-documented decarboxylation or decarbonylation of α-keto acids, the mechanistic studies revealed that α-keto acids went through a novel carbon–carbon bond cleavage resulting in the key gem-dinitroalkane intermediates, which were further transformed to nitrile oxides for the following 1,3-dipolar cycloadditions.
Recommended Journals
Related Literature
Sulfate ion encapsulation in caged supramolecular structures assembled by second-sphere coordination
Jianjun Liang, Jin Yang, Chuandong Jia, Hongrui Zhang, Ning Tang, Christoph Janiak
2008-02-11
Communication
DOI: 10.1039/B719019K
Asymmetric oxidation of sulfides under solvent-free or highly concentrated conditions
Kazuhiro Matsumoto, Tetsufumi Yamaguchi, Tsutomu Katsuki
2008-02-05
Communication
DOI: 10.1039/B719265G
An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters
Chris V. Galliford, Karl A. Scheidt
2008-03-10
Communication
DOI: 10.1039/B801597J
Phase-transfer dynamic combinatorial chemistry
Ruth Pérez-Fernández, Michael Pittelkow, Ana M. Belenguer, Jeremy K. M. Sanders
2008-01-03
Communication
DOI: 10.1039/B718075F
Self-assembly of a peptide rod–coil: a polyproline rod and a cell-penetrating peptide Tat coil
You-Rim Yoon, Yong-beom Lim, Eunji Lee, Myongsoo Lee
2008-03-11
Communication
DOI: 10.1039/B719868J
A new NCN pincer ruthenium complex and its catalytic activity for enantioselective hydrogenation of ketones
Jun-ichi Ito, Satoshi Ujiie, Hisao Nishiyama
2008-03-12
Communication
DOI: 10.1039/B800387D
Preparation of silyl substituted crotylzinc reagents and their highly diastereoselectiveaddition to carbonyl compounds
Matthew D. Helm, Peter Mayer, Paul Knochel
2008-03-19
Communication
DOI: 10.1039/B802157K
Synthesis and reactivity of tetrakis(imino)pyracene (TIP) ligands; bifunctional analogues of the BIAN ligand class
Kalyan V. Vasudevan, Michael Findlater, Alan H. Cowley
2008-03-03
Communication
DOI: 10.1039/B719251G
A near-infrared dye for multichannel imaging
Wellington Pham, Lauren Cassell, Amelie Gillman, Dmitry Koktysh, John C. Gore
2008-02-28
Communication
DOI: 10.1039/B719028J
You might also like
Compound Q&A
What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?
N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...
52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A
What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?
When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...
1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A
What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?
Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...
628-39-7Diethyldiselane
Compound Q&A
What is the market or research trend for oxocopper (CAS: 12053-18-8)?
The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...
12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A
What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?
The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...
1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A
What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?
2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...
35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A
What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?
2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...
91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A
How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?
(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...
129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A
What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?
3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...
4857-42-53-Methyl-1,2-oxazole...
Compound Q&A
How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?
Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...
1281816-04-3Lys-SMCC-DM1
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
![1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure](https://static.chemtradehub.com/structs/603/60373-71-9-7dfb.webp "1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure")
1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
CAS Number:
60373-71-9
Molecular Formula:
C19H19N3O
2-Methyl-2-propanyl 2-carbamimidoyl-1-piperidinecarboxylate
CAS Number:
1258640-98-0
Molecular Formula:
C11H21N3O2
![N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine structure](https://static.chemtradehub.com/structs/234/23446-03-9-e1e5.webp "N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine structure")
N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine
CAS Number:
23446-03-9
Molecular Formula:
C12H22N2O5S
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.