Synthesis and bromodemercuration of some permercurated arenes

1976 ◽  
Vol 29 (3) ◽  
pp. 627 ◽  
Author(s):  
GB Deacon ◽  
GJ Farquharson
Keyword(s):  
Good Yield ◽  
Benzene Derivative ◽  
Phenylmercuric Chloride ◽  
Methoxybenzoic Acid

Pentabromonitrobenzene, pentabromobenzoic acid, pentabromobenzamide, pentabromoacetanilide, barium pentabromobenzenesulphonate, 1,2,4,5 - tetrabromo -3-chloro-6-(trifluoromethyl)benzene, 2,3,5,6-tetrabromo-4-methoxytoluene 2,3,5,6-tetrabromo-4-methoxybenzamide, methyl 2,3,5,6-tetra- bromo-4-methoxybenzoate, and 1,2,5-tribromo-3,4-dichloro-6-fluorobenzene have been synthesized in good yield by bromodemercuration of the corresponding fully mercurated (permercurated) arenes, e.g. C6(HgO2CCF3)5NO2, which were prepared by reaction of an excess of molten mercuric tri- fluoroacetate with suitable arenes at c. 180-245�. Permercuration of p-methoxybenzoic acid was accompanied by complete decarboxylation giving, after bromodemercuration, pentabromo(methoxy)- benzene, which was also obtained in low yield from preparations of methyl 2,3,5,6-tetrabromo-4- methoxybenzoate and 2,3,5,6-tetrabromo-4-methoxybenzamide. Conditions have been devised for conversion of phenylmercuric chloride into either a pentamercurated or a hexamercurated benzene derivative, and hence into pentabromo-or hexabromobenzene. The results establish permercuration/bromodemercuration as a simple and versatile route to polybromobenzene.

Nickel-Catalyzed Inter- and Intramolecular Carbon-Sulfur Bond Metathesis by Reversible Arylation

2019 ◽  
Author(s):  
Tristan Delcaillau ◽  
Alessandro Bismuto ◽  
Zhong Lian ◽  
Bill Morandi
Keyword(s):  
Good Yield ◽  
Functional Group ◽  
Product Formation ◽  
Single Bond ◽  
Ring Closing Metathesis ◽  
Catalytic Systems ◽  
Metathesis Reactions ◽  
New Applications ◽  
Further Development ◽  
Sulfur Bond

A nickel-catalyzed carbon-sulfur bond metathesis has been developed to access high-value thioethers. 1,2-bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional group tolerant reaction. Further, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis which does not involve alkene bonds. In-depth organometallic studies support a reversible Ni(0)-Ni(II) pathway to product formation. Overall, this work does not only disclose a more sustainable and more functional group tolerant alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information which are highly relevant to the further development and application of unusual single bond metathesis reactions.

Efficient CDI/CH3SO3H -Catalyzed, Microwave-Assisted Synthesis of 2-Substituted Benzothiazoles

2018 ◽  
Vol 16 (1) ◽  
pp. 34-39
Author(s):  
Yao-Wei Li ◽  
Pei-Ming Zhang ◽  
Rui Li ◽  
Yan Bai ◽  
Yu Yu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Carboxylic Acids ◽  
1H Nmr ◽  
Good Yield ◽  
Microwave Assisted Synthesis ◽  
Synthetic Method ◽  
Benzothiazole Derivatives ◽  
Microwave Assisted ◽  
Highly Effective

CDI combined with CH3SO3H was found to be highly effective for the cyclization of 2-aminothiophenol derivatives with carboxylic acids under MW condition. Fourteen benzothiazole derivatives were synthesized in good yield and their structures were characterized by 1H-NMR, 13CNMR, IR and mass spectrometry. This simple, rapid synthetic method is believed to provide a useful process for the synthesis of 2-substituted benzothiazole compounds.

Relations between Structure and Antituberculotic Activity of 4-Alkoxybenzoic Acids

1993 ◽  
Vol 58 (1) ◽  
pp. 191-196 ◽  
Author(s):  
Karel Waisser ◽  
Jiří Kuneš ◽  
Jiří Klimeš ◽  
Miroslav Polášek ◽  
Želmíra Odlerová
Keyword(s):  
Active Compound ◽  
Antimycobacterial Activity ◽  
Methoxybenzoic Acid

Antimycobacterial activity of a series of alkoxybenzoic acids including 4-methoxybenzoic acid (II), 4-ethoxybenzoic acid (III), 4-propoxybenzoic acid (IV), 4-butoxybenzoic acid (V), 4-pentoxybenzoic acid (VI), 4-allyloxybenzoic acid (IX), 4-isopropoxybenzoic acid (VII), 4-isobutoxybenzoic acid (VIII) and 4-benzyloxybenzoic acid (X) has been determined and found to increase with the lipophilicity of the compounds expressed by the corresponding HPLC capacity factors. Also determined were the pKa values of the compounds mentioned. The most active compound, 4-pentoxybenzoic acid (VI), is comparable with commercial antituberculotics when tested in vitro.

The reaction of carboxylic acids with epoxides using lithium naphthalenide

1974 ◽  
Vol 27 (10) ◽  
pp. 2205 ◽  
Author(s):  
T Fujita ◽  
S Watanabe ◽  
K Suga
Keyword(s):  
Carboxylic Acids ◽  
Good Yield ◽  
Hydroxy Acids

Lithium naphthalenide reacts with carboxylic acids in the presence of diethylamine to give the α-anions of lithium carboxylates. Reaction of these anions with various epoxides gives the corresponding y-hydroxy acids in good yield. The γ-hydroxy acids easily cyclize to give γ-butyrolactones.

scholarly journals 2-Hydroxy-3-methoxybenzoic acid attenuates mast cell-mediated allergic reaction in mice via modulation of the FcεRI signaling pathway

2016 ◽  
Vol 38 (1) ◽  
pp. 90-99 ◽  
Author(s):  
Yeon-Yong Kim ◽  
In-Gyu Je ◽  
Min Jong Kim ◽  
Byeong-Cheol Kang ◽  
Young-Ae Choi ◽  
...  
Keyword(s):  
Mast Cell ◽  
Allergic Reaction ◽  
Signaling Pathway ◽  
Methoxybenzoic Acid

scholarly journals Direct Amidation to Access 3-Amido-1,8-Naphthalimides Including Fluorescent Scriptaid Analogues as HDAC Inhibitors

Cells ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1505
Author(s):  
Kyle N. Hearn ◽  
Trent D. Ashton ◽  
Rameshwor Acharya ◽  
Zikai Feng ◽  
Nuri Gueven ◽  
...  
Keyword(s):  
Optical Properties ◽  
Histone Deacetylase ◽  
Good Yield ◽  
Hdac Inhibitors ◽  
Selective Inhibitor ◽  
Imaging Studies ◽  
Highly Active ◽  
Theranostic Applications ◽  
New Compounds ◽  
Direct Amidation

Methodology to access fluorescent 3-amido-1,8-naphthalimides using direct Buchwald–Hartwig amidation is described. The protocol was successfully used to couple a number of substrates (including an alkylamide, an arylamide, a lactam and a carbamate) to 3-bromo-1,8-naphthalimide in good yield. To further exemplify the approach, a set of scriptaid analogues with amide substituents at the 3-position were prepared. The new compounds were more potent than scriptaid at a number of histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in a whole cell tubulin deacetylation assay where the inhibitors were more active than the established HDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compounds make them amenable to cellular imaging studies and theranostic applications.

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