![6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine structure](https://static.chemtradehub.com/structs/120/1203499-17-5-b4d1.webp "6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine structure")
6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine
CAS Number:
1203499-17-5
Molecular Formula:
C7H7BrN2O
Interrupting the Nazarov reaction: domino and cascade processes utilizing cyclopentenyl cations
Literature Information
Publication Date
2009-08-21
DOI
10.1039/B908515G
Impact Factor
6.222
Authors
Tina N. Grant, Curtis J. Rieder, Frederick G. West
View Original
Abstract
The Nazarov reaction entails the electrocyclic closure of a conjugated pentadienyl cation to furnish a cyclopentenyl cation. In its conventional protocol, this intermediate is allowed to undergo elimination through loss of an adjacent proton, providing cyclopentenone products. This feature article describes a relatively new class of domino and cascade processes in which the mechanistic course of the Nazarov reaction is diverted at the point of the cyclopentenyl cation intermediate, collectively referred to as “interrupted Nazarov reactions.” A variety of intra- or intermolecular nucleophiles, including silyl hydrides, alkenes, arenes, amines, halides, oxygen nucleophiles and azides, can capture the cation at one terminus, resulting in interesting polycyclic structures. 1,3-Dienes also trap the cyclopentenyl cation, but in this case via concerted [4 + 3]-cycloaddition to give keto-bridged cyclooctenes. An alternative method for generating the pentadienyl cyclization precursor from dichlorocyclopropanes rather than cross-conjugated dienones is also discussed, along with some novel trapping processes.
Related Literature
Towards understanding secondary structure transitions: phosphorylation and metal coordination in model peptides
Malgorzata Broncel, Sara C. Wagner, Kerstin Paul, Christian P. R. Hackenberger, Beate Koksch
2010-03-29
Paper
DOI: 10.1039/C001458C
Intrinsic acidity and electrophilicity of gaseous propargyl/allenyl carbocations
Priscila M. Lalli, Yuri E. Corilo, Patrícia V. Abdelnur, Marcos N. Eberlin
2010-03-29
Paper
DOI: 10.1039/C001985B
[Pb9CdCdPb9]6−: A Zintl cluster anion with an unsupported cadmium–cadmium bond
Binbin Zhou, Mark S. Denning, Thomas A. D. Chapman, John E. McGrady, Jose M. Goicoechea
2009-10-22
Communication
DOI: 10.1039/B917185A
Porous graphenes: two-dimensional polymer synthesis with atomic precision
Marco Bieri, Matthias Treier, Jinming Cai, Kamel Aït-Mansour, Pascal Ruffieux, Oliver Gröning, Pierangelo Gröning, Marcel Kastler, Ralph Rieger, Xinliang Feng, Klaus Müllen
2009-09-11
Communication
DOI: 10.1039/B915190G
Long wavelength red fluorescent dyes from 3,5-diiodo-BODIPYs
Lijuan Jiao, Changjiang Yu, Timsy Uppal, Mingming Liu, Yan Li, Yunyou Zhou, Erhong Hao, Xiaoke Hu, M. Graça H. Vicente
2010-04-14
Communication
DOI: 10.1039/C001068E
Synthesis of oligoribonucleotides with phosphonate-modified linkages
Ondřej Páv, Ivana Košiová, Ivan Barvík, Radek Pohl, Miloš Buděšínský, Ivan Rosenberg
2011-06-15
Paper
DOI: 10.1039/C1OB05488K
Stereoselective synthesis of enynones via base-catalyzed isomerization of 1,5-disubstituted-2,4-pentadiynyl silyl ethers or their alcohol derivatives
Jingjin Chen, Guoqin Fan, Yuanhong Liu
2010-09-16
Communication
DOI: 10.1039/C0OB00344A
Copper(i)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core
Ilaria Proietti Silvestri, Fikre Andemarian, George N. Khairallah, Su Wan Yap, Tim Quach, Sammi Tsegay, Craig M. Williams, Richard A. J. O'Hair, Paul S. Donnelly, Spencer J. Williams
2011-06-03
Paper
DOI: 10.1039/C1OB05360D
Linear and nonlinear photophysics and bioimaging of an integrin-targeting water-soluble fluorenylprobe
Alma R. Morales, Gheorghe Luchita, Ciceron O. Yanez, Mykhailo V. Bondar, Olga V. Przhonska
2010-04-08
Paper
DOI: 10.1039/B925934A
Elaboration and properties of hierarchically structured optical thin films of MIL-101(Cr)
Patricia Horcajada, Christian Serre, Cédric Boissière, David Grosso, Clément Sanchez, Gérard Férey
2009-10-29
Communication
DOI: 10.1039/B915011K
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
Chemical Communications
CiteScore:
8.6
Self-citation Rate:
4.7%
Articles per Year:
2458
ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular 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.