7341-96-0Relevant articles and documents
Synthesis of propiolamide and 1H, 13C and 15N NMR spectra of formamide, acetamide and propiolamide
Ferris, Thomas D.,Lee, Peter T.,Farrar, Thomas C.
, p. 571 - 576 (1997)
A high-yield synthesis and purification of propiolamide is described. The structure and purity of the compound were confirmed by 1H, 13C and 15N NMR studies. Natural abundance 13C and 15N chemical shift measurements in 3.0 M acetonitrile solutions are reported along with 1H-1H, 1H-15N and 1H-13C spin coupling constants. Polarization transfer techniques were used for the 15N and 13C measurements. The propiolamide NMR parameters were compared with those for 3.0 M solutions of formamide and acetamide in acetonitrile solution. Measurements at 298 and 278 K indicated that for all three compounds there is still significant rotation about the carbon-nitrogen bond at room temperature.
Thiol-yne click reaction: an interesting way to derive thiol-provided catechols
Nador, Fabiana,Mancebo-Aracil, Juan,Zanotto, Duham,Ruiz-Molina, Daniel,Radivoy, Gabriel
, p. 2074 - 2082 (2021/01/29)
The hydrothiolation of activated alkynes is presented as an attractive and powerful way to functionalize thiols bearing catechols. The reaction was promoted by a heterogeneous catalyst composed of copper nanoparticles supported on TiO2 (CuNPs/TiO2) in 1,2-dichloroethane (1,2-DCE) under heating at 80 °C. The catalyst could be recovered and reused in three consecutive cycles, showing a slight decrease in its catalytic activity. Thiol derivatives bearing catechol moieties, obtained through a versatile Michael addition, were reacted with different activated alkynes, such as methyl propiolate, propiolic acid, propiolamide or 2-ethynylpyridine. The reaction was shown to be regio- and stereoselective towards anti-Markovnikov Z-vinyl sulfide in most cases studied. Finally, some catechol derivatives obtained were tested as ligands in the preparation of coordination polymer nanoparticles (CNPs), by taking the advantage of their different coordination sites with metals such as iron and cobalt.
Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction
Yadav, Dolly,Singh, Nem,Kim, Tae Wu,Kim, Jae Young,Park, No-Joong,Baeg, Jin-Ook
supporting information, p. 2677 - 2685 (2019/06/13)
The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.
Advanced Continuous Flow Platform for On-Demand Pharmaceutical Manufacturing
Zhang, Ping,Weeranoppanant, Nopphon,Thomas, Dale A.,Tahara, Kohei,Stelzer, Torsten,Russell, Mary Grace,O'Mahony, Marcus,Myerson, Allan S.,Lin, Hongkun,Kelly, Liam P.,Jensen, Klavs F.,Jamison, Timothy F.,Dai, Chunhui,Cui, Yuqing,Briggs, Naomi,Beingessner, Rachel L.,Adamo, Andrea
, p. 2776 - 2784 (2018/02/06)
As a demonstration of an alternative to the challenges faced with batch pharmaceutical manufacturing including the large production footprint and lengthy time-scale, we previously reported a refrigerator-sized continuous flow system for the on-demand production of essential medicines. Building on this technology, herein we report a second-generation, reconfigurable and 25 % smaller (by volume) continuous flow pharmaceutical manufacturing platform featuring advances in reaction and purification equipment. Consisting of two compact [0.7 (L)×0.5 (D)×1.3 m (H)] stand-alone units for synthesis and purification/formulation processes, the capabilities of this automated system are demonstrated with the synthesis of nicardipine hydrochloride and the production of concentrated liquid doses of ciprofloxacin hydrochloride, neostigmine methylsulfate and rufinamide that meet US Pharmacopeia standards.
Samarium-mediated intramolecular cross-couplings of an α,β-unsaturated N-acylpyrrole
Law, Katherine R.,McErlean, Christopher S.P.
supporting information, p. 3113 - 3116 (2016/07/06)
The first example of an α,β-unsaturated N-acylpyrrole undergoing a SmI2-mediated cyclization is reported. In contrast to other unsaturated units, the intermediate samarium enolate readily engages in aldol-type reactions, necessitating careful control of the reaction conditions.
ANTI-FIBROTIC PYRIDINONES
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Paragraph 0337, (2015/11/02)
This application relates to polycyclic compounds with a pyridinone or pyridinone derivative core including, substituted pyridinones, 5,6- and 6,6- bicyclic heterocycles and substituted pyridine-thiones. This application also discloses methods of preparing these polycyclic compounds, pharmaceutical compositions and medicaments comprising said compounds and methods to treat, prevent or diagnose diseases, disorders or conditions associated with fibrosis.
PROCESS FOR PREPARING N-H OR N-ALKYL 2-PROPYNAMIDE
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Paragraph 0043; 0044, (2014/03/25)
Disclosed is a method for the synthesis of N—H or N-alkyl 2-propynamides useful as intermediate in the manufacture of pharmaceutically active ingredients.
PROCESS FOR PREPARING N-H OR N-ALKYL 2-PROPYNAMIDE
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Page/Page column 7, (2014/03/26)
Disclosed is a method for the synthesis of N-H or N-alkyl 2-propynamides useful as intermediate in the manufacture of pharmaceutically active ingredients.
ANTI-FIBROTIC PYRIDINONES
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Paragraph 0586-0587, (2014/04/17)
Disclosed are pyridinone compounds, method for preparing these compounds, and methods for treating fibrotic disorders.
Continuous flow total synthesis of rufinamide
Zhang, Ping,Russell, M. Grace,Jamison, Timothy F.
, p. 1567 - 1570 (2015/02/19)
Small molecules bearing 1,2,3-triazole functionalities are important intermediates and pharmaceuticals. Common methods to access the triazole moiety generally require the generation and isolation of organic azide intermediates. Continuous flow synthesis provides the opportunity to synthesize and consume the energetic organoazides, without accumulation thereof. In this report, we described a continuous synthesis of the antiseizure medication rufinamide. This route is convergent and features copper tubing reactor-catalyzed cycloaddition reaction. Each of the three chemical steps enjoys significant benefits and has several advantages by being conducted in flow. The total average residence time of the synthesis is approximately 11 min, and rufinamide is obtained in 92% overall yield.
