254729-95-8Relevant academic research and scientific papers
Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents
Antony, Jesna,Mathai, Sindhu,Natarajan, Rakesh,P. Musthafa, Sumi,Rappai, John P.,S. Devaky, Karakkattu
supporting information, (2022/02/25)
We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.
Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
Roy, Sarabindu,Yadaw, Ajay,Roy, Subho,Sirasani, Gopal,Gangu, Aravind,Brown, Jack D.,Armstrong, Joseph D.,Stringham, Rodger W.,Gupton, B. Frank,Senanayake, Chris H.,Snead, David R.
supporting information, p. 82 - 90 (2022/01/28)
Pyrrolo[2,1-f][1,2,4]triazine (1) is an important regulatory starting material in the production of the antiviral drug remdesivir. Compound 1 was produced through a newly developed synthetic methodology utilizing simple building blocks such as pyrrole, chloramine, and formamidine acetate by examining the mechanistic pathway for the process optimization exercise. Triazine 1 was obtained in 55% overall yield in a two-vessel-operated process. This work describes the safety of the process, impurity profiles and control, and efforts toward the scale-up of triazine for the preparation of kilogram quantity.
Synthesis process of retegravir intermediate
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Paragraph 0005; 0020; 0021, (2021/03/11)
The invention relates to a synthesis process of a retegravir intermediate 7-iodine-4-amido pyrrolo [2,1-F] [1, 2, 4] triazine. The method comprises the following steps: by using pyrrole as an initialraw material, carrying out aldehyde groupintroduction through phosphorus oxychloride-DMF to obtain 2-aldehyde group pyrrole; preparing a 2-cyano key intermediate through ammonium sulfate, wherein thesteps is the key step of the process; cyclizing the cyano intermediate and formamidine acetate to prepare a 4-amino intermediate; reacting with NIS and adding iodine to prepare the target compound 7-iodine-4-amido pyrrolo [2,1-F] [1, 2, 4] triazine. The whole process has the advantages of simple and easily available raw materials, simple and easy operation, and very high economic value and socialbenefit.
Effect of aromatic π-bridges on molecular structures and optoelectronic properties of A-π-D-π-A small molecular acceptors based on indacenodithiophene
Chen, Yueju,Liang, Jingtang,Shen, Ping,Wang, Linqiao,Weng, Chao,Yu, Yufu
, (2020/12/02)
Investigation on the relationship between molecular structure and device performance is of great important to develop highly efficient A-π-D-π-A small molecular acceptors (SMAs). However, there is still lack of a complete and in-depth study on effects of
Investigating Alkylated Prodigiosenes and Their Cu(II)-Dependent Biological Activity: Interactions with DNA, Antimicrobial and Photoinduced Anticancer Activity
Colard-Thomas, Julien,Danz, Karin,Doniz Kettenmann, Sebastian,Kraft, Matilda,Kulak, Nora,Schwarz, Stefan,Wagner, Sylvia,White, Matthew,Wiehe, Arno,Wieland, Gerhard,Fe?ler, Andrea T.
supporting information, (2021/12/24)
Prodigiosenes are a family of red pigments with versatile biological activity. Their tripyrrolic core structure has been modified many times in order to manipulate the spectrum of activity. We have been looking systematically at prodigiosenes substituted
Visible-Light-Driven Oxidative Cleavage of Alkenes Using Water-Soluble CdSe Quantum Dots
Li, Jianing,Zhao, Jingnan,Ma, Cunfei,Yu, Zongyi,Zhu, Hongfei,Yun, Lei,Meng, Qingwei
, p. 4985 - 4992 (2021/10/16)
The oxidative cleavage of C=C bonds is an important chemical reaction, which is a popular reaction in the photocatalytic field. However, high catalyst-loading and low turnover number (TON) are general shortcomings in reported visible-light-driven reactions. Herein, the direct oxidative cleavage of C=C bonds through water-soluble CdSe quantum dots (QDs) is described under visible-light irradiation at room temperature with high TON (up to 3.7×104). Under the same conditions, water-soluble CdSe QDs could also oxidize sulfides to sulfoxides with 51–84 % yields and TONs up to 3.4×104. The key features of this photocatalytic protocol include high TONs, wide substrates scope, low catalyst loadings, simple and mild reaction conditions, and molecular O2 as the oxidant.
Neutrophil-Selective Fluorescent Probe Development through Metabolism-Oriented Live-Cell Distinction
Gao, Min,Lee, Sun Hyeok,Park, Sang Hyuk,Ciaramicoli, Larissa Miasiro,Kwon, Haw-Young,Cho, Heewon,Jeong, Joseph,Chang, Young-Tae
supporting information, p. 23743 - 23749 (2021/10/14)
Human neutrophils are the most abundant leukocytes and have been considered as the first line of defence in the innate immune system. Selective imaging of live neutrophils will facilitate the in situ study of neutrophils in infection or inflammation events as well as clinical diagnosis. However, small-molecule-based probes for the discrimination of live neutrophils among different granulocytes in human blood have yet to be reported. Herein, we report the first fluorescent probe NeutropG for the specific distinction and imaging of active neutrophils. The selective staining mechanism of NeutropG is elucidated as metabolism-oriented live-cell distinction (MOLD) through lipid droplet biogenesis with the help of ACSL and DGAT. Finally, NeutropG is applied to accurately quantify neutrophil levels in fresh blood samples by showing a high correlation with the current clinical method.
Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses
Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko
, p. 6504 - 6517 (2021/05/06)
The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.
Visible-light mediated facile dithiane deprotection under metal free conditions
Dharpure, Pankaj D.,Bhowmick, Anindita,Warghude, Prakash K.,Bhat, Ramakrishna G.
, (2019/12/09)
Visible light mediated facile and selective dithiane deprotection under metal free conditions is developed. Eosin Y (1 mol%) proved to be an effective catalyst for the dithiane deprotection under the ambient photoredox conditions. The standard household compact fluorescent light source (CFL bulb) proved to be effective under open-air conditions in aqueous acetonitrile at room temperature. The protocol that exhibits a broad substrate scope and functional group tolerance has been shown to expand to a range of transformations for the electron-rich and -deficient thioacetals and thioketals. The synthetic utility of this protocol has also been demonstrated by gram-scale application.
Molecularly Defined Manganese Catalyst for Low-Temperature Hydrogenation of Carbon Monoxide to Methanol
Ryabchuk, Pavel,Stier, Kenta,Junge, Kathrin,Checinski, Marek P.,Beller, Matthias
supporting information, p. 16923 - 16929 (2019/10/28)
Methanol synthesis from syngas (CO/H2 mixtures) is one of the largest manmade chemical processes with annual production reaching 100 million tons. The current industrial method proceeds at high temperatures (200-300 °C) and pressures (50-100 atm) using a copper-zinc-based heterogeneous catalyst. In contrast, here, we report a molecularly defined manganese catalyst that allows for low-temperature/low-pressure (120-150 °C, 50 bar) carbon monoxide hydrogenation to methanol. This new approach was evaluated and optimized by quantum mechanical simulations virtual high-throughput screenings. Crucial for this achievement is the use of amine-based promoters, which capture carbon monoxide to give formamide intermediates, which then undergo manganese-catalyzed hydrogenolysis, regenerating the promoter. Following this conceptually new approach, high selectivity toward methanol and catalyst turnover numbers (up to 3170) was achieved. The proposed general catalytic cycle for methanol synthesis is supported by model studies and detailed spectroscopic investigations.
