1-(5-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol
CAS Number:
1039827-16-1
Molecular Formula:
C8H5BrF4O
Rapid synthesis of hexahydropyrrolo[3,4-b]pyrrole-fused quinolines via a consecutive [3 + 2] cycloaddition and reduction/intramolecular lactamization cascade
Literature Information
Publication Date
2020-08-10
DOI
10.1039/D0QO00858C
Impact Factor
5.281
Authors
Yan-Liang Lin, Yun-Ta Lee, Yi-Ting Huang
View Original
Abstract
An unprecedented synthesis of novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines is achieved through the sequential [3 + 2] cycloaddition reaction of azomethine ylides with maleimides followed by intramolecular lactamization. Condensation of the α-amino acid methyl ester with 2-nitrobenzaldehyde leads to an ester stabilized azomethine ylide which further reacts with maleimide to form hexahydropyrrolo[3,4-c]pyrrole. After the reduction of a nitro group, an unusual transamidation reaction is observed, furnishing the novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines. Isolation of the hexahydropyrrolo[3,4-c]pyrrole amide intermediate revealed the pathway of the reaction mechanism.
Related Literature
Formation of a solid solution between [N(C2H5)4][BF4] and [N(C2H5)4][PF6] in crystal and plastic crystal phases
Kazuhiko Matsumoto, Ryojun Nonaka, Yushen Wang, Gleb Veryasov, Rika Hagiwara
2016-12-08
Paper
DOI: 10.1039/C6CP07992J
Electronic properties of layered phosphorus heterostructures
Ruge Quhe, Shenyan Feng, Ming Lei
2016-12-02
Paper
DOI: 10.1039/C6CP06583J
Molecular qubits based on potentially nuclear-spin-free nickel ions
K. Bader, S. H. Schlindwein, D. Gudat
2016-12-21
Paper
DOI: 10.1039/C6CP08161D
Probing nonlinear optical coefficients in self-assembled peptide nanotubes
Soma Khanra, Kartik Ghosh, Fabio F. Ferreira, Wendel A. Alves, Francesco Punzo, Ping Yu, Suchismita Guha
2017-01-04
Paper
DOI: 10.1039/C6CP07879F
Water-tunable solvatochromic and nanoaggregate fluorescence: dual colour visualisation and quantification of trace water in tetrahydrofuran
Masaru Tanioka, Atsuya Muranaka, Yoshinao Shirasaki, Yousuke Ooyama, Masashi Ueda
2016-11-11
Paper
DOI: 10.1039/C6CP06808A
Do primary carriers of both positive charge and unpaired electron spin exist in irradiated propylene carbonate?
2016-12-08
Communication
DOI: 10.1039/C6CP07477D
An unexpected bridge between chemical bonding indicators and electrical conductivity through the localization tensor
Ángel Martín Pendás, José Manuel Guevara-Vela, Daniel Menéndez Crespo, Aurora Costales, Evelio Francisco
2016-12-12
Paper
DOI: 10.1039/C6CP07617C
Effect of doping and chemical ordering on the optoelectronic properties of complex oxides: Fe2O3–V2O3 solid solutions and hetero-structures
Iffat H. Nayyar, Sara E. Chamberlin, Tiffany C. Kaspar, Niranjan Govind, Scott A. Chambers, Peter V. Sushko
2016-12-07
Paper
DOI: 10.1039/C6CP06087K
Substituent effects on the relaxation dynamics of furan, furfural and β-furfural: a combined theoretical and experimental approach
Sven Oesterling, Oliver Schalk, Ting Geng, Richard D. Thomas, Tony Hansson, Regina de Vivie-Riedle
2016-12-16
Paper
DOI: 10.1039/C6CP06240G
Intermolecular structure and hydrogen-bonding in liquid 1,2-propylene carbonate and 1,2-glycerol carbonate determined by neutron scattering
Yoan M. Delavoux, Mark Gilmore, Martin P. Atkins, Małgorzata Swadźba-Kwaśny, John D. Holbrey
2016-12-15
Paper
DOI: 10.1039/C6CP07790K
You might also like
Compound Q&A
Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?
2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...
7765-11-92-(2-chloroacetamido...
Compound Q&A
Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?
2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...
62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A
What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?
(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...
1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A
What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?
2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...
917985-54-72-(5-Hexylthiophen-2...
Compound Q&A
Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?
While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...
102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A
What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?
The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...
851376-80-2tert-butyl 3-hydroxy...
Compound Q&A
How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?
Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...
6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A
How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?
(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...
351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A
What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?
Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...
10065-79-9Dibenzyl carbonimido...
Compound Q&A
What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?
The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...
74228-83-4(beta,beta,2,3,4,5,6...
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
![19-[Chloro(dideuterio)methyl]-19-deuterio-20,20-dideuteriooxyoctatriacontane-18,21-dione structure](https://static.chemtradehub.com/structs/124/1246818-85-8-6244.webp "19-[Chloro(dideuterio)methyl]-19-deuterio-20,20-dideuteriooxyoctatriacontane-18,21-dione structure")
19-[Chloro(dideuterio)methyl]-19-deuterio-20,20-dideuteriooxyoctatriacontane-18,21-dione
CAS Number:
1246818-85-8
Molecular Formula:
C39H75ClO4
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.