1150-26-1Relevant articles and documents
Optimizing ring-opening polymerization of ε-caprolactone by using aluminum complexes bearing amide as catalysts and their application in synthesizing poly-ε-caprolactone with special initiators and other polycycloesters
Tseng, Hsi-Ching,Chen, Fu-Shen,Chiang, Michael Y.,Lu, Wei-Yi,Chen, Yu-Hsieh,Lai, Yi-Chun,Chen, Hsuan-Ying
, p. 90682 - 90690 (2015)
A series of aluminum complexes bearing amidate ligands, including acylamide, sulfonamide, and aryl carbamate, was synthesized. In addition, the optimization of ring-opening polymerization of ε-caprolactone by using these aluminum complexes as catalysts was studied. Polymerization results revealed that steric bulky groups in anilinyl groups decreased the catalytic activity of aluminum sulfonamide complexes but increased that of aluminum-acylamide complexes. Compared with other complexes bearing N-(4-methoxyphenyl) acylamidate and N-(4-methoxyphenyl) p-tolylsulfonamidate, an aluminum complex (MfOMeAlMe2) bearing methyl (4-methoxyphenyl)carbamate had the highest catalytic activity with an ideal molecular weight control and narrow polydispersity index (PDI). Other poly-ε-caprolactones with special end chains, such as PEG-200, 2-dimethylaminoethanol, bis(2-hydroxyethyl) disulfide, 2-((2-hydroxyethyl)disulfanyl)ethyl 2-bromo-2-methylpropanoate, and PEG-polyester-bearing disulfide group, were successfully synthesized using MfOMeAlMe2 as the catalyst. The polymerization of δ-valerolactone and 2-bromo-ε-caprolactone by using BnOH as an initiator and MfOMeAlMe2 as the catalyst resulted in poly-δ-valerolactone and poly-2-bromo-ε-caprolactone, respectively, with a precise molecular weight and a narrow PDI as well as poly-ε-caprolactones.
Nanocopper-mediated direct arylsulfonamidation of aryl halides with arylsulfonyl azides
Yavari,Solgi,Ghazanfarpour-Darjani,Ahmadian
, p. 977 - 981 (2012)
An efficient protocol for direct arylsulfonamidation of aryl iodides and aryl bromides using arylsulfonylazides catalyzed by copper nanoparticles is described. Iranian Chemical Society 2012.
Combustion-derived CdO nanopowder as a heterogeneous basic catalyst for efficient synthesis of sulfonamides from aromatic amines using p-toluenesulfonyl chloride
Anandakumar, Belladamadu Siddappa,Madhusudana Reddy, Muthukur Bhojegowd,Thipperudraiah, Kumarappa Veerappa,Pasha, Mohamed Afzal,Chandrappa, Gujjarahalli Thimmanna
, p. 135 - 144 (2013)
A simple and rapid synthesis of CdO nanopowder via the solution combustion route employing l-(+)-tartaric acid as a fuel is reported for the first time. The catalyst was characterized by PXRD, SEM, TEM, BET surface area measurement, basic site measurement from back titration and FTIR. Combustion derived CdO nanopowder acts as a catalyst in the sulfonylation of amines with p-toluenesulfonyl chloride to obtain sulfonamides in excellent yield (85-95 %) and high purity under mild reaction conditions. CdO nanopowder has been found to be an efficient catalyst requiring a shorter reaction time (10-30 min) to obtain sulfonamide when compared with the commercial CdO powder requiring 2 h under similar conditions. The catalyst can be recovered and reused four times without any significant loss of catalytic activity. Potential role of CdO nanopowder in the synthesis of sulfonamides and its mechanism is proposed.
Natural Indian Natrolite zeolite-supported Cu nanoparticles: A new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions
Azarifar, Davood,Soleimanei, Fatemeh
, p. 12119 - 12126 (2014)
We report here on the preparation of primary sulfonamides and efficient, easily recoverable and reusable copper nanoparticles supported on natural Indian Natrolite zeolite as a catalyst for arylation of sulfonamides with arylboronic acids in water. The catalyst was characterized using the powder XRD, SEM, EDS and FT-IR spectroscopy. The significant advantages of this methodology are high yields, elimination of organic solvents, and simple work-up procedure. The catalyst was easily isolated from the reaction mixture and reused with no significant loss in its activity.
Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Alikarami, Mohammad
, p. 143 - 148 (2010)
An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.
Straightforward synthesis, spectroscopic characterizations and comprehensive DFT calculations of novel 1-ester 4-sulfonamide-1,2,3-triazole scaffolds
Alizadeh, Maryam,Mirjafary, Zohreh,Saeidian, Hamid
, (2020)
For the first time, an efficient click azide?alkyne [3 + 2] cycloaddition reaction for synthesis of new 1-ester 4-sulfonamide-1,2,3-triazole derivatives was developed via a three-component reaction of N-propargylsulfonamides, sodium azide, and α-haloesters in a one pot method. The mild reaction conditions, avoiding the isolation of hazardous organic azides, good yields (65–78%), and commercially available and inexpensive starting materials are advantages of this cycloaddition reaction for synthesis of fine chemicals. The all desired products were characterized by FT-IR, 1H and 13C NMR spectroscopy. The HOMO-LUMO analysis (electrophilicity index), vibrational frequencies (FT-IR), 1H and 13C chemical shift values and Li+ and Na+ ion affinities of a desired product have been also calculated by density functional theory (DFT). Lithium ion affinity of the product was determined as 80.78 kJ/mol higher than its sodium ion affinity. The NICS index was used to confirm of the cation π interaction in complex of the synthesized product with Li+ and Na+ ions.
A convenient and benign synthesis of sulphonamides in PEG-400
Das, Pranab Jyoti,Sarmah, Bhaskar
, p. 189 - 191 (2015)
A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.
A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**
Wei, Mingjie,Liang, Dacheng,Cao, Xiaohui,Luo, Wenjun,Ma, Guojian,Liu, Zeyuan,Li, Le
supporting information, p. 7397 - 7404 (2021/02/16)
A broad-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1-hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram-scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.
KCC-1 aminopropyl-functionalized supported on iron oxide magnetic nanoparticles as a novel magnetic nanocatalyst for the green and efficient synthesis of sulfonamide derivatives
Azizi, Sajjad,Shadjou, Nasrin,Hasanzadeh, Mohammad
, (2019/11/22)
A new magnetic nanocatalyst (Fe3O4@KCC-1-npr-NH2) was synthesized directly through the reaction of Fe3O4@KCC-1 with (3-aminopropyl) triethoxysilane (APTES) using a hydrothermal protocol. Prepared nanocomposite was used as a magnetically reusable nanocatalyst for an efficient synthesis of a broad range of sulfonamide derivatives in water as a green solvent at room temperature and the products are collected by filtration with excellent yields (85–97%). The nanocatalyst could be remarkably recovered and reused after ten times without any significant decrease in activity. This mild and simple synthesis method offers some advantages including short reaction time, high yield and simple work-up procedure.
