Synthesis of new 4[4-(4-nitrophenoxy)phenyl]-5-substituted-2H-1,2,4-triazole-3-thiones and their evaluation as anthelmintics

Namratha, B; Bilehal, Dinesh; ShyamKumar, V.; Gaonkar, Santosh L.

doi:10.1007/s11164-015-2123-1

Cited by 5 publications

(10 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The absorption peak at 1496 cm −1 , corresponding to C N of TPA may be credited to complete double N-arylation of the 4-nitrophenoxy aniline. 17 A complete transformation of A1 into A is evidenced by the FTIR spectra of both compounds. In the FTIR spectrum of triamine A, two spikes appeared at 3351 and 3427 cm −1 , ascribed to the primary amine (N H stretching vibrations).…”

Section: Resultsmentioning

confidence: 94%

Thermally resistant, mechanically stable, and processable triphenylamine‐based hyperbranched copolyimides

Khalid

Siddiqi

Park

2020

J of Applied Polymer Sci

View full text Add to dashboard Cite

A trifunctional, triamine 4-(4-aminophenoxy)-4 0 ,4 00-diamino triphenylamine (A) was successfully synthesized by N-arylation in the presence of cesium fluoride, followed by catalytic reduction. A series of aromatic tree-shaped hyperbranched copolyimides (HBPIs, 1-4) was fruitfully synthesized by onepot polycondensation of a newly synthesized triamine monomer (A), difunctional monomer 4,4 0-dianiline, 4,4 0-oxydianiline (ODA) and a series of aromatic dianhydride monomers. The appropriate molar ratio of triamine, ODA to the dianhydride monomer B is 1:1:2.5 for HBPIs synthesis using the A 2 A 3 B 5 type copolymerization approach. The synthesized HBPIs exhibited a moderate number-average molecular weight (25,700-28,400 g/mol) and polydispersity in the range 2.6-3.0 as revealed by gel permeation chromatography measurement. The oxidative thermal degradation analyses of the HBPIs showed that the synthesized materials are thermally stable up to 500 C and glass transition temperature in the range 290-302 C. The elongation at break was found in the range 4.8%-8.1% as revealed by tensile measurement. Besides, good thermal stability the HBPIs exhibited excellent flow, appreciable organosolubility, easy processability, and noticeable mechanical stability, thus suggesting their use as thermally resistant, protective coatings for various devices and outdoor environment in the future.

show abstract

Section: Resultsmentioning

confidence: 94%

Thermally resistant, mechanically stable, and processable triphenylamine‐based hyperbranched copolyimides

Khalid

Siddiqi

Park

2020

J of Applied Polymer Sci

View full text Add to dashboard Cite

show abstract

“…General experimental procedure for the synthesis of 1,2,4triazolidine-3-thiones and structure elucidation of novel 1,2,4triazolidine-3-thiones using IR, 1 H and 13 C NMR and Mass is provided in the supporting information. Sulfamic acid [23] (20) EtOH Reflux 30 92 2 [C 16 MPy]AlCl 3 Br [25] (10) H 2 O RT 10 96 3 Catalyst free [31] EtOH 80 15 94 4 N,N-dimethylpyridine-4-amine [24] (20) H 2 O RT 20 95 5 Catalyst free [29] PEG Catalyst free [30] Glycerol 40 96 95 9…”

Section: Supporting Information Summarymentioning

confidence: 99%

“…[21] In view of the diverse applications of 1,2,4-triazole and its synthetic congeners, a plethora of methods have been reported for their synthesis. [22] Amongst these, the simplest approach for the synthesis of 1,2,4-triazolidine-3-thiones involves the reaction of aldehydes or ketones with thiosemicarbazides in the presence of catalysts such as sulfamic acid, [23] N,N-dimethylpyridine-4-amine, [24] [C 16 MPy]AlCl 3 Br, [25] [(Py) 2 SO] [HSO 4 ], [26] [HMPBSA]HSO 4 , [27] glycine nitrate. [28] Moreover, organic solvents like PEG-400, [29] glycerol [30] and ethanol [31] endorsing catalyst free conditions have also been reported.…”

Section: Introductionmentioning

confidence: 99%

“…Aza heterocyclic compounds are the key scaffolds in the process of identification of novel drug molecules. Among these, 1,2,4‐triazoles fused with thione has garnered tremendous attention due to their promising therapeutic properties including antibacterial, antitumor, antitubercular, anticonvulsant, anti‐inflammatory, antidepressant, antioxidant, anti‐lipid peroxidation, antimicrobial, anticancer, anthelmintic activity, β ‐glucuronidase enzyme inhibition activity etc. The molecular hybrids from Ciprofloxacin and 1,2,4‐triazole‐3‐thione have displayed promising antibacterial activities .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Thiamine Hydrochloride Catalyzed Synthesis of 1,2,4‐Triazolidine‐3‐thiones in Aqueous Medium

et al. 2019

View full text Add to dashboard Cite

In the present work, the catalytic potential of natural organocatalyst thiamine hydrochloride is explored for the synthesis of 1,2,4‐triazolidine‐3‐thiones in aqueous medium. The reaction of thiosemicarbazides with various substrates viz aryl/ heteroaryl aldehydes, isatins, cyclic and aromatic ketones to obtain corresponding 1,2,4‐triazolidine‐3‐thiones have been successfully demonstrated for the first time. The method proposed in this work addresses the green chemistry principles such as biodegradable catalyst, ambient reaction condition, shorter reaction time, high yield of the products, recyclability of catalyst and high atom economy.

show abstract

“…This process mainly covers preparation of aldehyde by Darzen reaction. Further to our studies on active pharmaceutical ingredients and biologically active heterocycles [12][13][14][15][16], we report herein industrially scalable, efficient total synthesis of donepezil hydrochloride by using safe reagents and experimental conditions. To confirm the product and to study the structural conformation details, the crystal structure of 2-(1benzylpiperidin-4-ylmethyliden)-5,6-dimethoxyindan-1-one, an intermediate in the synthesis of donepezil is also reported.…”

mentioning

confidence: 99%

Industrially Scalable Synthesis of Anti-alzheimer Drug Donepezil

Gaonkar¹,

Nadaf²,

Bilehal³

et al. 2017

Asian J. Chem.

Self Cite

View full text Add to dashboard Cite

Alzheimer's disease, a type of dementia has no cure, over the time leads to death. It is a chronic neurodegenerative disease, commonly starts slowly and gets worse over time [1]. The symptoms of this disease are the gradual progress of absent-mindedness, trouble in language, mutism and perplexity [2]. Stepwise deterioration in remembrance and consciousness is the symptomatic course of the ailment [3]. Scientists believe that Alzheimer's disease may result from a deficiency of neurotransmitters present in brain nerves. Donepezil is an oral medication for Alzheimer's disease [4]. It belongs to cholinesterase inhibitors class of drugs with fewer side effects [5-8]. Donepezil inhibits acetylcholinesterase [9], an enzyme responsible for the destruction of acetylcholine, a neurotransmitter [10]. Research on donepezil began in 1983 with its first Phase I clinical trial in 1989 [11]. Besides, it has studied in patients with Down's syndrome, multiple sclerosis and schizophrenia. In most of these patents, indanone was used as the starting material for the preparation of donepezil HCl. US Patent US 4,895,841 described that indanone was reacted with aldehyde by aldol condensation by using a base like LDA at-80 °C and heating the reaction mixture at room temperature to conduct dehydration which is reduced by Pd/C to yield donepezil. EP 0296560B1 discloses 1-indanon-2-yl-phosphonate with an aldehyde (Wittig reaction), which was reduced with Pd/C. US 5,606,064 discloses a process where indanone was condensed with N-benzyl pyridine-4-carboxaldehyde, which on treatment

show abstract

Synthesis of new 4[4-(4-nitrophenoxy)phenyl]-5-substituted-2H-1,2,4-triazole-3-thiones and their evaluation as anthelmintics

Cited by 5 publications

References 20 publications

Thermally resistant, mechanically stable, and processable triphenylamine‐based hyperbranched copolyimides

Thermally resistant, mechanically stable, and processable triphenylamine‐based hyperbranched copolyimides

Thiamine Hydrochloride Catalyzed Synthesis of 1,2,4‐Triazolidine‐3‐thiones in Aqueous Medium

Industrially Scalable Synthesis of Anti-alzheimer Drug Donepezil

Contact Info

Product

Resources

About