5271-67-0Relevant articles and documents
Three step, one-pot process to prepare thiophene-2-carbonyl chloride (TCC), a key raw material in the manufacture of tioxazafen (Nemastrike)
Walker, Daniel P.,Graham, Charles R.,Miller, William H.,Koeller, Kevin J.
, p. 834 - 838 (2019)
Nematodes are parasitic organisms that cause significant damage to crops. Tioxazafen (Nemastrike), is a proprietary seed treatment being developed by Bayer AG as a broad-spectrum nematicide. Thiophene-2-carbonyl chloride (TCC) is the key raw material in the manufacture of tioxazafen. Current manufacturing routes to TCC suffer from byproduct formation and significant waste generation, which leads to high manufacturing cost. A potentially more cost-effective process for preparing TCC from commercial thiophene has been developed. The advantages of this new chemical approach are illustrated in the processing details described in this Letter.
Synthesis and Antitumor Activities of Resveratrol Derivatives on Cervical Cancer Hela Cells
Jin, Lu,Ren, Yu-Jie,Du, Cheng
, p. 652 - 655 (2015)
Using 2-thiophenecarbonyl chloride and 2-furoyl chloride to modify the structure of the natural product resveratrol, we synthesized five novel resveratrol derivatives. The target compounds were evaluated for their antitumor activities against cervical cancer HeLa cells by the MTT method. The results indicated that the compound 3a displayed the best antitumor activities, which is higher than the value of resveratrol, and its inhibition ratio was 95.1% against HeLa cells at the concentration of 75 μmol/L.
Direct observation of fluorescent complex formation of acridinium-anilide-thiophene triad with poly-L-glutamic acid
Hu, Jingqiu,Joshi, Monica,Elioff, Michael
, p. 59 - 69 (2017)
Conformational changes and self-assembly process of polypeptides and proteins are important for biological processes. In order to investigate such changes, we prepared a fluorescent probe, thiophene-phenylanilide-acridinium triad, and investigated its pho
Novel analogues of ebselen - Preparation of 2-alkylthieno[2,3-d]isoselenazol-3(2H)-ones by peroxide-mediated ring-closure of 3,3′-diselenobis(N-alkylthiophencarboxamides)
Laws, Melissa J.,Schiesser, Carl H.,White, Jonathan M.,Zheng, Shi-Long
, p. 277 - 283 (2000)
Studies toward the preparation of novel thiophen analogues of the anti-inflammatory compound Ebselen are presented. We report that treatment of 3,3′-diselenobis(N-alkylthiophen-2-carboxamides) (13; R = Me, Pri, But, Ph) with benzoyl peroxide in benzene under reflux affords the corresponding 2-alkylthieno[2,3-d]isoselenazol-3(2H)-ones (7) in 10-73% yield, except for the phenyl derivative (13; R = Ph) which proved too insoluble to react. Irradiation of the PTOC imidate esters of 2-benzylseleno-N-butylthiophen-3-carboxamide (9) and 3-benzylseIeno-N-butylthiophen-2-carboxamide (12) provides none of the expected Ebselen analogues. This failure to ring-close is discussed in terms of conformational rigidity in amidyl radicals (22) and (23). CSIRO 2000.
One-step Conversion of Amides and Esters to Acid Chlorides with PCl3
Li, Fangshao,Wu, Xiaofang,Guo, Fengzhe,Tang, Zi-Long,Xiao, Jing
supporting information, p. 4314 - 4317 (2021/07/16)
A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.
Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters
Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.
supporting information, p. 7915 - 7922 (2021/05/03)
A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.
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.
Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis
De La Higuera Macias, Maximiliano,Arndtsen, Bruce A.
supporting information, p. 10140 - 10144 (2018/08/23)
We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.
A General Cp*CoIII-Catalyzed Intramolecular C?H Activation Approach for the Efficient Total Syntheses of Aromathecin, Protoberberine, and Tylophora Alkaloids
Lerchen, Andreas,Knecht, Tobias,Koy, Maximilian,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 12149 - 12152 (2017/09/13)
Herein, we report a Cp*CoIII-catalyzed C?H activation approach as the key step to create highly valuable isoquinolones and pyridones as building blocks that can readily be applied in the total syntheses of a variety of aromathecin, protoberberine, and tylophora alkaloids. This particular C?H activation/annulation reaction was achieved with several terminal as well as internal alkyne coupling partners delivering a broad scope with excellent functional group tolerance. The synthetic applicability of this protocol reported herein was demonstrated in the total syntheses of two Topo-I-Inhibitors and two 8-oxyprotoberberine cores that can be further elaborated into the tetrahydroprotoberberine and the protoberberine alkaloid core. Moreover these building blocks were also transformed to six different tylophora alkaloids in expedient fashion.
PROCESSES FOR THE PREPARATION OF HETEROARYL CARBOXYLIC ACIDS
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Paragraph 0190 - 0195, (2018/04/20)
Provided herein are processes for the preparation of heteroaryl carboxylic acids.
