Efficient Synthesis of Chromones with Alkenyl Functionalities by the Heck Reaction

2010 ◽  
Vol 63 (11) ◽  
pp. 1582 ◽  
Author(s):  
Tamás Patonay ◽  
Attila Vasas ◽  
Attila Kiss-Szikszai ◽  
Artur M. S. Silva ◽  
José A. S. Cavaleiro
Keyword(s):  
Heck Reaction ◽  
Halogen Atom ◽  
Phase Transfer ◽  
Bromine Atom ◽  
Tetrabutylammonium Bromide ◽  
Phase Transfer Catalyst ◽  
Efficient Synthesis ◽  
Terminal Alkenes

The usefulness of the Heck reaction in the field of chromones has been demonstrated. Bromochromones with the halogen atom in their rings A and B were reacted with various terminal alkenes to give hitherto unknown alkenyl‐substituted chromones. Reactivity of the substrates was found to markedly depend on the position of the bromine atom. Under phosphine‐free conditions using a phase‐transfer catalyst additive (tetrabutylammonium bromide), shorter reaction periods and usually higher yields were obtained.

Rapid and efficient synthesis of metal-free phthalocyanine derivatives

2006 ◽  
Vol 10 (11) ◽  
pp. 1253-1258 ◽  
Author(s):  
Ahmad Shaabani ◽  
Ali Maleki
Keyword(s):  
Ionic Liquid ◽  
Microwave Irradiation ◽  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Efficient Synthesis ◽  
Metal Free ◽  
High Yields ◽  
Short Times

Metal-free phthalocyanine derivatives have been synthesized in very short times with high yields in the presence of 1,1,3,3-tetramethylguanidinium trifluoroacetate (TMGT) as an ionic liquid or tetrabutylammonium bromide (TBAB) as a phase transfer reagent under both classical heating conditions and using microwave irradiation. The best results were obtained with ionic liquid. Both the ionic liquid and phase transfer reagent can be recycled for subsequent reactions and reused without appreciable loss of efficiency.

scholarly journals First and efficient synthesis of 4-[((3,4-dihydroxybenzoyl)-oxy)methyl]-phenyl-β-D-glucopyranoside, an antioxidant from Origanum vulgare

2016 ◽  
Vol 81 (1) ◽  
pp. 23-28
Author(s):  
Yu-Wen Li ◽  
Cui-Li Ma
Keyword(s):  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
Efficient Synthesis ◽  
Origanum Vulgare ◽  
Triethylbenzylammonium Chloride ◽  
Polyphenolic Glycoside ◽  
Hydroxybenzyl Alcohol ◽  
Methyl Phenyl

4-(3,4-Dihydroxybenzoyloxymethyl)phenyl-O-?-D-glucopyranoside (DBPG, 1 ), a polyphenolic glycoside previously isolated from Oregano(Origanum vulgare L.) in 0.08% isolated yield, was synthesized in five chemical steps with 41.4% overall yield. First, 4-(hydroxymethylphenyl)-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside 4 was obtained in 53.2% yield by selective glycosylation of 4-hydroxybenzyl alcohol 3 with 2,3,4,6-tetra-O-acetyl-?-D-glucopyranosyl bromide 2 in a mixture of chlorobenzene and aqueous CsOH using triethylbenzylammonium chloride (TEBAC) as a phase transfer catalyst. Then, this product was esterified with 3,4-diacetoxylbenzoyl chloride 7 to generate 4-(3,4-diacetoxybenzoyloxy-methyl) phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside 8 in 95% yield. Finally, selectively global deacetylation of 8 was performed in a mixture of dibutyltin oxide and methanol under reflux to afford 1 in 94.8% yield.

scholarly journals Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5918
Author(s):  
Bimal Krishna Banik ◽  
Bubun Banerjee ◽  
Gurpreet Kaur ◽  
Shivam Saroch ◽  
Rajat Kumar
Keyword(s):  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Catalytic Amount ◽  
Coupling Reactions ◽  
Efficient Synthesis ◽  
Organic Transformations ◽  
Co Catalyst ◽  
Oxidation Reduction ◽  
Recent Developments ◽  
Significant Attention

During the last two decades, tetrabutylammonium bromide (TBAB) has gained significant attention as an efficient metal-free homogeneous phase-transfer catalyst. A catalytic amount of TBAB is sufficient to catalyze various alkylation, oxidation, reduction, and esterification processes. It is also employed as an efficient co-catalyst for numerous coupling reactions. It has also acted as an efficient zwitterionic solvent in many organic transformations under molten conditions. In this review, we have summarized the recent developments on TBAB-catalyzed protocols for the efficient synthesis of various biologically promising heterocyclic scaffolds.

The Photooxidative Desulfurization of Thiophene with Tetrabutylammonium Bromide as a Phase Transfer Catalyst

2010 ◽  
Vol 28 (11) ◽  
pp. 1140-1146 ◽  
Author(s):  
F. T. Li ◽  
D. S. Zhao ◽  
R. H. Liu ◽  
Z. J. Jin ◽  
Z. M. Sun
Keyword(s):  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Phase Transfer Catalyst

Simultaneous immobilization of a matrix containing palladium and phase transfer catalyst on silica nanoparticles: application as a recoverable catalyst for the Heck reaction in neat water

RSC Advances ◽  
2014 ◽  
Vol 4 (40) ◽  
pp. 20704-20708 ◽  
Author(s):  
Abdol R. Hajipour ◽  
Ghobad Azizi
Keyword(s):  
Silica Nanoparticles ◽  
Palladium Catalyst ◽  
Heck Reaction ◽  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
Phosphonium Salts ◽  
Neat Water ◽  
Recoverable Catalyst ◽  
Reaction In Water ◽  
Simultaneous Immobilization

Simultaneous anchoring of phosphonium salts and palladium catalyst on silica nanoparticles and the application in the Heck reaction in water is described.

ChemInform Abstract: Efficient Synthesis of Sulfones Using Polysorbate-80 as Phase-Transfer Catalyst.

ChemInform ◽  
2010 ◽  
Vol 23 (5) ◽  
pp. no-no
Author(s):  
G. K. BISWAS ◽  
M. CHAKRABARTY ◽  
P. BHATTACHARYYA
Keyword(s):  
Phase Transfer ◽  
Phase Transfer Catalyst ◽  
Polysorbate 80 ◽  
Efficient Synthesis

Eco-Friendly Approach for the Synthesis of Thiophene Linked Benzothiazepines as Biocompatible Free Radical Scavengers

2021 ◽  
Vol 6 (1) ◽  
pp. 1-6
Author(s):  
P. Sudeep ◽  
K.R. Raghavendra ◽  
R. Sowmya ◽  
K. Ajay Kumar
Keyword(s):  
Free Radical ◽  
Hydroxyl Radical ◽  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Radical Scavenging ◽  
Phase Transfer Catalyst ◽  
Free Radical Scavengers ◽  
Radical Scavengers ◽  
Citrus Juice

A series of new thiophene tethered benzothiazepines (5a-h) were synthesized through citrus juice mediated (4+3) annulations of thienyl chalcones with 2-aminobenzenethiol in the presence of tetrabutylammonium bromide as phase transfer catalyst under reflux conditions. The synthesized compounds were characterized by spectroscopic and CHN analysis. To check the antioxidant potentials of the synthesized compounds, in vitro DPPH and hydroxyl radical scavenging assays were conducted. The results shows that amongst the series, compounds 5b with (21.44-49.72%) and (16.88-42.60%); 5c with (24.88-56.00%) and (22.33-53.12%); and 5h with (22.80-47.10%) and (15.33-44.12%) excellent DPPH and hydroxyl radical potencies comparable with the respective standards used in the experiments.

scholarly journals Triton-B Mediated Efficient Synthesis of Thioxoimidazolidine-4,5-diones

2019 ◽  
Vol 32 (1) ◽  
pp. 183-186
Author(s):  
Ram Kishore ◽  
M. Kamboj ◽  
M. Shukla ◽  
Devdutt Chaturvedi
Keyword(s):  
Room Temperature ◽  
Phase Transfer ◽  
Oxalyl Chloride ◽  
Phase Transfer Catalyst ◽  
Efficient Synthesis

A simple, mild and efficient protocol for the synthesis of thioxoimidazolidine-4,5-diones (1-15) from substituted thiourea employing Triton-B/CS2 system has been discussed. The protocol described is an easy, efficient, nature-friendly method using cheap, easily available, less toxic reagents at room temperature. The synthesis involves the reaction between substituted thiourea in toluene and oxalyl chloride at room temperature using phase transfer catalyst Triton-B/CS2 system.

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