Tandem oxidative radical brominative addition of activated alkynes and spirocyclization: switchable synthesis of 3-bromocoumarins and 3-bromo spiro-[4,5] trienone
Literature Information
Publication Date
2016-02-18
DOI
10.1039/C6QO00041J
Impact Factor
5.281
Authors
Guanyinsheng Qiu, Tong Liu, Qiuping Ding
View Original
Abstract
A K2S2O8-mediated tandem radical brominative addition of alkynoates, oxidative spiro-cyclization, and 1,2-migration of esters is reported for the synthesis of 3-bromocoumarins with high efficiency. The prepared 3-bromocoumarins are successfully converted into 3-alkynyl and 3-phosphite coumarins under mild conditions. The synthesis of a specific bromo-incorporated spiro-[4,5]trienyl-2,8-dione is achieved under the same conditions when N-methyl-N,3-diphenylpropiolate is used as the substrate.
Related Literature
Immortal ring-opening polymerization of ε-caprolactone by a neat magnesium catalyst system: an approach to obtain block and amphiphilic star polymers in situ
Bo Liu, Dongtao Liu, Xinli Liu, Dongmei Cui
2014-05-20
Paper
DOI: 10.1039/C4PY00384E
Synthesis of end-functionalized boronic acid containing copolymers and their bioconjugates with rod-like viruses for multiple responsive hydrogels
2014-05-15
Paper
DOI: 10.1039/C4PY00508B
Mesogen-jacketed liquid crystalline polymers with peripheral oligo(ethylene oxide) chains: phase structure and thermoresponsive behavior
Qian Tan, Junqiu Liao, Sheng Chen, Ya Zhu, Hailiang Zhang
2014-05-09
Paper
DOI: 10.1039/C4PY00371C
How does a tiny terminal alkynyl end group drive fully hydrophilic homopolymers to self-assemble into multicompartment vesicles and flower-like complex particles?
Tingting Liu, Wei Tian, Yunqing Zhu, Yang Bai, Hongxia Yan, Jianzhong Du
2014-05-06
Paper
DOI: 10.1039/C4PY00501E
Dimanganese decacarbonyl/2-cyanoprop-2-yl-1-dithionaphthalate: toward sunlight induced RAFT polymerization of MMA
Xuelang Miao, Jiajia Li, Zhengbiao Zhang, Zhenping Cheng, Wei Zhang, Jian Zhu, Xiulin Zhu
2014-04-23
Paper
DOI: 10.1039/C4PY00509K
Thermoresponsive properties of 3-, 4-, 6-, and 12-armed star-shaped poly[2-(dimethylamino)ethyl methacrylate]s prepared by core-first group transfer polymerization
Seiya Kikuchi, Yougen Chen, Keita Fuchise, Kenji Takada, Junsuke Kitakado, Shin-ichiro Sato, Toshifumi Satoh, Toyoji Kakuchi
2014-04-09
Paper
DOI: 10.1039/C4PY00290C
Supramolecular flower micelle formation of polyrotaxane-containing triblock copolymers prepared from macro-chain transfer agents bearing molecular hooks
Atsushi Tamura, Hajime Tanaka, Nobuhiko Yui
2014-05-16
Paper
DOI: 10.1039/C4PY00379A
Facile fabrication of reduction-responsive nanocarriers for controlled drug release
Rui Sun, Qiaojie Luo, Chen Gao, Ying Wang, Lilong Gao, Hong Du, Ying Huang, Xiaodong Li, Zhiquan Shen, Weipu Zhu
2014-06-03
Communication
DOI: 10.1039/C4PY00577E
Synthesis and phase behavior of a new 2-vinylbiphenyl-based mesogen-jacketed liquid crystalline polymer with a high glass transition temperature and low threshold molecular weight
Qi-Kai Zhang, Hai-Jian Tian, Yu-Feng Zhu, Yongri Liang, Zhihao Shen, Xing-He Fan
2014-03-11
Paper
DOI: 10.1039/C3PY01755A
You might also like
Compound Q&A
What is Ethyl 3-cyclohexylpropanoate (CAS: 10094-36-7)?
Ethyl 3-cyclohexylpropanoate is a clear, colorless to light yellow liquid with a...
10094-36-7Ethyl 3-cyclohexylpr...
Compound Q&A
How should waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl)nicotinic acid (CAS: 34783-31-8) be handled?
Waste containing 2-(Hydroxymethyl)-5-(methoxycarbonyl)-6-methyl-4-(2-nitrophenyl...
34783-31-82-(Hydroxymethyl)-5-...
Compound Q&A
How should waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) be handled?
Waste containing 2,4,6-Tris(pentafluoroethyl)-1,3,5-triazine (CAS: 858-46-8) sho...
858-46-82,4,6-Tris(pentafluo...
Compound Q&A
What precautions should be taken when handling Chloroac-nle-oh (CAS: 56787-36-1)?
When handling Chloroac-nle-oh (CAS: 56787-36-1), it is essential to wear appropr...
56787-36-1Chloroac-nle-oh
Compound Q&A
What industries use Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate (CAS: 752244-05-6)?
Ethyl 6-phenylimidazo[2,1-b][1,3]thiazole-3-carboxylate is primarily used in the...
752244-05-6Ethyl 6-phenylimidaz...
Compound Q&A
Are there alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis?
Alternatives to alpha-(2-Bromophenyl)benzylamine (CAS: 55095-15-3) in synthesis ...
55095-15-3alpha-(2-Bromophenyl...
Compound Q&A
How should waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) be handled?
Waste containing 2-Chloro-5-methoxypyridine (CAS: 139585-48-1) should be managed...
139585-48-12-Chloro-5-methoxypy...
Compound Q&A
What industries use 1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9)?
1-(4-Methoxyphenyl)-2,5-dimethyl-1H-pyrrole (CAS: 5044-27-9) is used in various ...
5044-27-91-(4-Methoxyphenyl)-...
Compound Q&A
Are there alternatives to 3-Bromo-5-(N-Boc)aminomethylisoxazole (CAS: 903131-45-3) in synthesis?
There are alternative reagents and compounds that can be used in the synthesis o...
903131-45-33-Bromo-5-(N-Boc)ami...
Compound Q&A
What is Tungsten(IV) oxide (CAS: 12036-22-5)?
Tungsten(IV) oxide, also known as tungsten dioxide, is a chemical compound with ...
12036-22-5Tungsten(IV) oxide
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
![3-[(4-Nitrobenzyl)oxy]-3-oxopropanoic Acid structure](https://static.chemtradehub.com/structs/773/77359-11-6-0d04.webp "3-[(4-Nitrobenzyl)oxy]-3-oxopropanoic Acid structure")
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.