1372783-28-2Relevant articles and documents
A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst
Karami, Mostafa,Zare, Abdolkarim
, p. 289 - 293 (2018)
A solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).
Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahy-dropyridines using a nanostructured silica-based catalyst under mild conditions
Irannejad-Gheshlaghchaei, Navid,Sajadikhah, Seyed Sajad
, p. 1251 - 1260 (2021/07/25)
Aim and Objective: Nano-2-[N',N'-dimethyl-N'-(silica-n-propyl)ethanaminium chlo-ride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4 ]) was used as a highly effective and heterogeneous silica-based nanostructured catalyst for the synthesis of 1-thioamidoalkyl-2--naphthols and substituted tetrahydropyridines. Material and Methods: The expected products were prepared in mild conditions. In this work, three novel 1-thioamidoalkyl-2-naphthols and two new tetrahydropyridine derivatives were synthe-sized and characterized by IR,1H and13C NMR and Mass spectroscopy. Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioace-tamide catalyzed by nano-[DSPECDA][HSO4 ] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehy-des and ethylacetoacetate under solvent-free and mild conditions. Conclusion: The reaction results were found to be better compared to the literature in terms of one or more of these factors: yield, time, and the reaction media. All the products were purified by re-crystallization from EtOH, and without column chromatography, being in good agreement with the green chemistry protocols.
Choline peroxydisulfate oxidizing Bio-TSIL: Triple role player in the one-pot synthesis of Betti bases and gem-bisamides from aryl alcohols under solvent-free conditions
Gadilohar, Balu L.,Kumbhar, Haribhau S.,Shankarling, Ganapati S.
, p. 4647 - 4657 (2015/06/16)
The one-pot, multicomponent solvent-free synthesis of Betti bases (amidoalkyl naphthols) and gem-bisamides directly from alcohol is proposed by an eco-friendly approach using a new environmentally benign, biodegradable, oxidizing, and task-specific ionic liquid (bio-TSIL), namely, choline peroxydisulfate monohydrate (ChPS) 1. Choline bisulphate (ChBS) 2 reduced species is then generated in situ from 1, which catalyses the formation of the desired products in a shorter reaction time with good to excellent yields. This bio-TSIL 1 plays a triple role as an oxidant, catalyst and solvent. It is easily recycled and can be reused five times.
1,3-Dibromo-5,5-dimethylhydantoin as an efficient catalyst for synthesis of thioamidoalkyl and bis(thio)amidoalkyl-2-naphthols under solvent-free conditions
Ghorbani-Choghamarani, Arash,Rashidimoghadam, Shima
, p. 6271 - 6281 (2015/08/18)
Abstract An efficient and easy method for one-pot three-component synthesis of thioamidoalkyl and bis(thio)amidoalkyl naphthols by condensation of aromatic aldehydes, 2-naphthol, and acetamide or thioacetamide under thermal condition at 130°C in the presence of 1,3-dibromo-5,5-dimethylhydantoin is described. The present approach offers several advantages such as reduced reaction time, higher yield, and economic availability of the catalyst.
Catalytic application of N,2-dibromo-6-chloro-3,4-dihydro-2 H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide on the synthesis of 1-carbamato-alkyl-2-naphthols and 1-thioamido-alkyl-2-naphthols
Khazaei, Ardeshir,Abbasi, Fatemeh,Moosavi-Zare, Ahmad Reza
, p. 364 - 372 (2015/06/22)
A novel N-bromo sulfonamide reagent, namely N, 2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide, is prepared and employed as a new and highly efficient catalyst for the preparation of 1-carbamato-alkyl-2-naphthol and 1-thioamido-alkyl-2-naphthol derivatives.
Condensation of Aryl Aldehydes, 2-naphthol, and Thioacetamide Catalyzed by N-halo Reagents in Neutral Media
Khazaei, Ardeshir,Abbasi, Fatemeh,Moosavi-Zare, Ahmad Reza,Khazaei, Marzieh,Beyzavi, M. Hassan
, p. 850 - 854 (2015/10/29)
A new three-component, highly efficient and solvent-free approach for the synthesis of known and new 1-thioamido-alkyl-2-naphthol derivatives was investigated. This was achieved via a one-pot condensation by reacting aryl aldehydes, 2-naphthol, and thioacetamide in the presence of catalytic amount of 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (TCCA) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH). Mechanistically, the in situ generation of Cl+ ion from TCCA and DCDMH is proposed to catalyse the reactions in neutral media. In the presented work, most of the products have been reported for the first time.
A three-component novel synthesis of 1-[aryl(thioacetamido)methyl]-2- naphthol derivatives
Hassanabadi, Alireza,Hosseini-Tabatabaei, Mohammad R.
, p. 510 - 511 (2012/10/29)
A three-component reaction between 2-naphthol, an aryl aldehydes and thioacetamide catalysed by p-toluenesulfonic acid under reflux conditions provided a simple and efficient one-pot route for the synthesis of 1-[aryl(thioaceta mido)methyl]-2-naphthol derivatives in excellent yields.
Synthesis of novel thioamidoalkyl- and thiocarbamidoalkyl naphthols via a three-component condensation reaction using heterogeneous catalyst of ferric hydrogensulfate
Eshghi, Hossein,Zohuri, Gholam Hossein,Damavandi, Saman
experimental part, p. 516 - 525 (2011/12/15)
Ferric hydrogensulfate [Fe(HSO4)3] was used as a suitable heterogeneous catalyst for the one-pot multicomponent reaction of b-naphthol, aromatic aldehydes, and thioamide derivatives to obtain the corresponding thioamidoalkyl naphthols. Various novel thioamidoalkyl naphthols and thiocarbamidoalkyl naphthols were synthesized in good yields from thioacetamide and thiourea. The heterogeneous nature of the catalyst made it reusable for further chemical reactions.Copyright Taylor & Francis Group, LLC.
