53392-49-7Relevant academic research and scientific papers
Design, synthesis and antitrypanosomal activities of 2,6-disubstituted-4,5,7-trifluorobenzothiophenes
Bhambra, Avninder S.,Edgar, Mark,Elsegood, Mark R.J.,Li, Yuqi,Weaver, George W.,Arroo, Randolph R.J.,Yardley, Vanessa,Burrell-Saward, Hollie,Krystof, Vladimir
, p. 347 - 353 (2016)
Current treatments for Human African Trypanosomiasis (HAT) are limited in their application, have undesirable dosing regimens and unsatisfactory toxicities highlighting the need for the development of a safer drug pipeline. Our medicinal chemistry program
Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions
Dong, Ya,Li, Ruining,Zhou, Junliang,Sun, Zhankui
supporting information, p. 6387 - 6390 (2021/08/23)
Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.
Continuous Flow Synthesis of 2H-Thiopyrans via thia-Diels–Alder Reactions of Photochemically Generated Thioaldehydes
Sachse, Florian,Gebauer, Konrad,Schneider, Christoph
, p. 64 - 71 (2020/11/30)
Herein, we report a novel protocol for the photochemical generation of thioaldehydes in a continuous flow process which were in situ reacted with electron rich 1,3-butadienes in thia-Diels–Alder reactions. A broad range of 3,6-dihydro-2H-thiopyrans were formed as products in much higher yields and productivities as compared to classical batch processes. Moreover, greatly reduced reaction times and a facile large-scale preparation of products were achieved by fully exploiting the advantages of continuous flow technology.
Visible-light induced metal-free cascade Wittig/hydroalkylation reactions
Miao, Pannan,Li, Ruining,Lin, Xianfeng,Rao, Liangming,Sun, Zhankui
supporting information, p. 1638 - 1641 (2021/03/09)
Cascade reactions are green and powerful transformations for building multiple carbon-carbon bonds in one step. Through a relay olefination and radical addition process, we were able to develop the cascade Wittig/hydroalkylation reactions induced by visible light. This metal-free radical approach features mild conditions, robustness, and excellent functionality compatibility. It allows access to saturated C3 homologation products directly from aldehydes or ketones. The synthetic utility of this method is demonstrated by a two-step synthesis ofindolizidine 209D.
Synthesis of β-oxo carbonyl and thiocarbonyl compounds via basic sulfur abstraction
Silva, Saúl,Maycock, Christopher D.
, (2019/09/10)
Sulfur abstraction from suitable thioesters represents a mild method for the formation of carbon-carbon bonds and the formation of 1,3-dicarbonyl compounds. A study of the scope and limitations of this reaction for the synthesis of these or mixed 1,3-carbonyl/thiocarbonyl compounds by a base promoted sulfur abstraction rearrangement is described. These reactions were typically very clean and the products were obtained in good yield (65–95%) in just 30 min. This method is particularly efficient for the introduction of thiocarbonyl containing groups. Thus, it constitutes a synthetic strategy for the generation of a new carbon-carbon bond and the regioselective preparation of mixed β-dicarbonyl compounds.
Intermolecular Phosphite-Mediated Radical Desulfurative Alkene Alkylation Using Thiols
Lopp, John M.,Schmidt, Valerie A.
supporting information, p. 8031 - 8036 (2019/10/19)
We report herein the development of a S atom transfer process using triethyl phosphite as the S atom acceptor that allows thiols to serve as precursors of C-centered radicals. A range of functionalized and electronically unbiased alkenes including those containing common heteroatom-based functional groups readily participate in this reductive coupling. This process is driven by the exchange of relatively weak S-H and C-S bonds of aliphatic thiols for C-H, C-C, and S-P bonds of the products formed.
Br?nsted-base-catalyzed remote cascade reactivity of 2,4-dienones-asymmetric synthesis of tetrahydrothiophenes
Przydacz, Artur,Kowalczyk, Rafa?,Albrecht, ?ukasz
supporting information, p. 9566 - 9569 (2017/11/30)
This study demonstrates that the remote cascade functionalization of 2,4-dienones can be realized by employing Br?nsted base catalysis. The developed cascade involving 1,6-addition followed by the intramolecular aldol reaction provides a straightforward a
α-Methylphenacyl thioesters as convenient thioacid precursors
Hatanaka, Toru,Yuki, Ryosuke,Saito, Ryota,Sasaki, Kaname
supporting information, p. 10589 - 10592 (2016/11/30)
α-Methylphenacyl (Mpa) thioesters are described as precursors of thioacids. Mpa thioesters are accessible via the condensation of carboxylic acids and phenacyl thiol, which is easily prepared without column chromatography. The Mpa thioesters are selectively deprotected by reduction with zinc dust in the presence of conventional thioacid protecting groups. In addition, the Mpa group exhibits orthogonal reactivity to the Boc group. These features are expected to facilitate the preparation of complex thioacids, including those in peptides.
Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate
Venkateswararao, Eeda,Jalani, Hitesh B.,Manoj,, Manickam,Jung, Sang-Hun
supporting information, p. 1449 - 1456 (2016/09/24)
Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.
Stereoselective one-pot synthesis of β-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions
Heredia, Adrian A.,Soria-Castro, Silvia M.,Bouchet, Lydia M.,Oksdath-Mansilla, Gabriela,Barrionuevo, Cecilia A.,Caminos, Daniel A.,Bisogno, Fabricio R.,Argueello, Juan E.,Penenory, Alicia B.
, p. 6516 - 6526 (2014/08/18)
A stereoselective one-pot procedure was developed to prepare S-substituted (Z)-enol esters through a base-triggered rearrangement. This transition metal-free multicomponent approach can be performed under an air atmosphere at room temperature, tolerates a wide set of chemical functionalities and generally affords high isolated yields. The (Z)-selectivity arises from the [1,4]-S- to O-acyl migration. the Partner Organisations 2014.
