scholarly journals Sulfonic acid heterogeneous catalysts for dehydration of C6-monosaccharides to 5-hydroxymethylfurfural in dimethyl sulfoxide

2014 ◽  
Vol 35 (5) ◽  
pp. 644-655 ◽  
Author(s):  
Gabriel Morales ◽  
Juan A. Melero ◽  
Marta Paniagua ◽  
Jose Iglesias ◽  
Blanca Hernández ◽  
...  
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sulfonic Acid ◽  
Heterogeneous Catalysts

Synthesis of fatty 1,2,4-trioxanes by peracetalisation of β-hydroxy hydroperoxides

Synthesis ◽  
2021 ◽  
Author(s):  
Thomas De Dios Miguel ◽  
Dan Louvel ◽  
Killian Onida ◽  
Adeline Lavoignat ◽  
Stephane Picot ◽  
...  
Keyword(s):  
Sulfonic Acid ◽  
Heterogeneous Catalysts ◽  
Antimalarial Activity ◽  
Acid Catalyst ◽  
Methyl Tert Butyl Ether ◽  
Significant Activity ◽  
Butyl Ether ◽  
Aliphatic Aldehydes ◽  
Toluene Sulfonic Acid ◽  
Optimized Conditions

The peracetalisation of a β-hydroxy hydroperoxide derived from methyl oleate was studied using benzaldehyde as a model substrate to give the corresponding fatty 1,2,4-trioxane. The desired product was obtained as a mixture of regioisomers but only one diastereoisomer of each was formed. The nature of the acid catalyst was studied and both para-toluene sulfonic acid (PTSA) and Amberlyst A35 (A35) were found to be efficient homogeneous and heterogeneous catalysts, respectively. The nature of the solvent was also investigated and ethereal solvents such as 2-methyltetrahydrofuran (2-MeTHF), methyl tert-butyl ether (MTBE) and cyclopentyl methyl ether (CPME) gave the best NMR yield (85%) for the preparation of the fatty trioxane. The optimized conditions were applied to a range of aromatic and aliphatic aldehydes and the corresponding 1,2,4-trioxanes were isolated with 30-91% yields (21 examples). The antimalarial activity of 3 trioxanes was studied against Plasmodium falciparum, however, no significant activity was detected (IC50 > 1600 nM).

N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIII. Cleavage and Rearrangement Reactions of Pyrazolo[1,5-b][1,2,4,6]thiatriazine 1,1-Dioxides

2016 ◽  
Vol 69 (1) ◽  
pp. 61 ◽  
Author(s):  
Rebecca E. Norman ◽  
Michael V. Perkins ◽  
Andris J. Liepa ◽  
Craig L. Francis
Keyword(s):  
Ethyl Acetate ◽  
Dimethyl Sulfoxide ◽  
Trifluoroacetic Acid ◽  
Sulfonic Acid ◽  
Trifluoroacetic Anhydride ◽  
Ring Cleavage ◽  
Thermal Rearrangement ◽  
Heterocyclic Synthesis ◽  
Similar Treatment ◽  
Catalytic Hydrogenolysis

Treatment of pyrazolo[1,5-b][1,2,4,6]thiatriazines 1 with the Vilsmeier–Haack reagent afforded pyrazolo[1,5-a][1,3,5]triazines 5. Reaction of compounds 1 with trifluoroacetic anhydride, dimethyl sulfoxide, and triethylamine afforded 5-dimethylsulfanylidene derivatives 8. The guanidino-pyrazole-sulfonic acid 9 was produced from treatment of compounds 1 with trifluoroacetic acid under anhydrous conditions. Similar treatment in the presence of water afforded the desulfonated pyrazolo-guanidine 6. Reactions of 6 with one-carbon electrophiles provided various 4-substituted pyrazolo[1,5-a][1,3,5]triazines 5. Attempted catalytic hydrogenolysis of N7-benzyl pyrazolo[1,5-b][1,2,4,6]thiatriazines 2 in alcohols led to sulfamates 12 from thiatriazine ring cleavage. Ethyl acetate or tert-butanol as solvent allowed successful debenzylation to provide compounds 1. Aminolysis of compounds 2 gave sulfamides 13. Thermal rearrangement of compounds 2 afforded 6-benzyl-pyrazolo[3,4-e][1,2,4]thiadiazines 14.

Cu(0) onto sulfonic acid functionalized silica/carbon composites as bifunctional heterogeneous catalysts for the synthesis of polysubstituted pyridines and nitriles under benign reaction media

RSC Advances ◽  
2016 ◽  
Vol 6 (101) ◽  
pp. 99604-99614 ◽  
Author(s):  
Madhvi Bhardwaj ◽  
Manmeet Kour ◽  
Satya Paul
Keyword(s):  
Sulfonic Acid ◽  
Heterogeneous Catalysts ◽  
Carbon Composites ◽  
Functionalized Silica ◽  
One Pot ◽  
Oxidative Transformation ◽  
One Pot Synthesis ◽  
The One ◽  
Reaction Media

Bifunctional heterogeneous catalysts based on Cu(0) onto sulphonated silica/carbon composites for the one-pot synthesis of polysubstituted pyridines and oxidative transformation of aldehydes to nitriles.

Sulfonic acid-functionalized organic knitted porous polyaromatic microspheres as heterogeneous catalysts for biodiesel production

2018 ◽  
Vol 42 (15) ◽  
pp. 12745-12753 ◽  
Author(s):  
Anuraj Varyambath ◽  
Mi-Ra Kim ◽  
Il Kim
Keyword(s):  
Vegetable Oils ◽  
Sulfonic Acid ◽  
Heterogeneous Catalysts ◽  
Biodiesel Production ◽  
Highly Active

Sulfonic acid functionalized porous polyaromatics are highly active and recyclable heterogeneous catalysts for biodiesel production from vegetable oils.

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