63329-72-6Relevant academic research and scientific papers
Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction
Formánek, Bed?ich,Tauchman, Ji?í,Císa?ová, Ivana,Vesely, Jan
, p. 8510 - 8521 (2020/07/16)
The present report describes an organocatalytic cascade reaction between 2-alkylidene benzo[b]thiophenone derivatives and enones in the presence of the Cinchona alkaloid amine. Spirobenzothiophenonic cyclohexane derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.
Competitive cascade cyclization of 2′-tosyloxychalcones: An easy access to thioflavones and thioaurones
Venkateswarlu, Somepalli,Murty, Gandrotu Narasimha,Satyanarayana, Meka,Siddaiah, Vidavalur
supporting information, p. 2347 - 2354 (2020/07/03)
A new and efficient approach for the synthesis of thioflavones and thioaurones by competitive cascade cyclization of 2′-tosyloxychalcones has been developed. 2′-Tosyloxychalcones were smoothly converted into thioflavones and thioaurones by incorporation of sulfur atom using elemental sulfur and triethylamine in DMSO with good yields. The advantages of the methodology are the formation of both thioflavones and thioaurones in a single step. Easily accessible substrates, mild reaction conditions and compatibility with a broad range of functional groups make this protocol clean and inexpensive.
METHOD FOR SYNTHESIZING THIOAURONES
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, (2021/02/12)
An embodiment of the present invention is a process for producing 2 - benzoic acid compound by reacting a thiosalicylic acid with a strongly basic substance and a benzylhalide. The 2 - methoxy - N N-methyl -2 - benzamides, which are reacted with N - methoxy - N N-methylcarbamoyl chloride to produce N - methoxy-N-methylbenzamides. The N - methoxy - N N-methyl -2 - (benzocyclohexyl) benzamide is treated with arylethynyl salt to prepare 1 - (2- benzocyclohexyl) phenyl -3 - phenyl -2 - profin -1 . The 1 - (2-) phenyl -3 - phenyl -2 - profin -1 - one is treated with an acid material. Provided is a method for preparing a thiouronone compound.
Cooperative Activating Effect of Tertiary Amine/DMSO on Elemental Sulfur: Direct Access to Thioaurones from 2′-Nitrochalcones under Mild Conditions
Nguyen, Thanh Binh,Retailleau, Pascal
supporting information, p. 186 - 189 (2018/01/17)
A new mode for the activation of elemental sulfur is reported. In the presence of both DMSO and a tertiary aliphatic amine (triethylamine or N-methylpiperidine), this element reacts directly with a wide range of 2′-nitrochalcones 1 to provide the corresponding thioaurones 2 in high yields even at room temperature and in the absence of transition metal catalyst.
Isomer-Specific Hydrogen Bonding as a Design Principle for Bidirectionally Quantitative and Redshifted Hemithioindigo Photoswitches
Zweig, Joshua E.,Newhouse, Timothy R.
supporting information, p. 10956 - 10959 (2017/08/21)
A new class of bidirectionally quantitative photoswitches based on the hemithioindigo (HTI) scaffold is reported. Incorporation of a pyrrole hydrogen-bond donor leads to a bathochromic shift allowing for quantitative bidirectional isomerization. Additionally, extending conjugation from the electron-rich pyrrole results in quantitative visible-light photoswitches, as well as photoswitches that isomerize with red and near-infrared light. The presence of the hydrogen bond leading to the observed redshift is supported by computational and spectroscopic evidence.
Iodine-catalyzed intramolecular oxidative thiolation of vinylic carbon-hydrogen bonds via tandem iodocyclization and dehydroiodination: Construction of 2-methylene-3-thiophenones
Zheng, Gang,Ma, Xiaoli,Liu, Bangyu,Dong, Ying,Wang, Mang
, p. 743 - 748 (2014/04/03)
A metal-free vinylic carbon-hydrogen bond thiolation has been developed. Under the catalysis of iodine (10 mol%), the cyclization of α-alkenoyl ketene dithioacetals afforded a broad range of polyfunctionalized 2-methylene-3-thiophenones in good selectivity with moderate to excellent yields via tandem iodocyclization and dehydroiodination. The synthetic strategy can also be extended to the cyclization of ortho-methylthiophenyl vinyl ketones leading to 2-methylene-3-benzothiophenones.
Making fast photoswitches faster - Using hammett analysis to understand the limit of donor-acceptor approaches for faster hemithioindigo photoswitches
Maerz, Benjamin,Wiedbrauk, Sandra,Oesterling, Sven,Samoylova, Elena,Nenov, Artur,Mayer, Peter,De Vivie-Riedle, Regina,Zinth, Wolfgang,Dube, Henry
supporting information, p. 13984 - 13992 (2016/02/18)
Hemithioindigo (HTI) photoswitches have a tremendous potential for biological and supramolecular applications due to their absorptions in the visible-light region in conjunction with ultrafast photoisomerization and high thermal bistability. Rational tail
One-step synthesis of thioaurones
Cabiddu, M. Grazia,Cabiddu, Salvatore,Cadoni, Enzo,De Montis, Stefania,Fattuoni, Claudia,Melis, Stefana,Usai, Michele
, p. 875 - 878 (2007/10/03)
A rapid, one-step preparation of 2-(arylmethylidene)-1-benzothiophen-3-ones (thioaurones) using directed α-metallation, ring closure and aldol-type condensation is described. The reaction leads exclusively to the Z-isomer.
Elimination, ring-contraction, and fragmentation reactions of 1-thioflavanone 1-oxides
Somogyi
, p. 1159 - 1165 (2007/10/03)
Epimeric thioflavanone sulfoxides (2b) were selectively transformed into thioflavone (1a), thioaurone (3a), and di(2-cinnamoylphenyl) disulfide (4). Disulfide 4 can be recyclized into thioaurones (3a-c) and thioflavanones (2a, 5) with heterolysis of the S - S bond. The 3-p-anisylidene sulfoxide analog of 2b (6) transforms, with fragmentation, into 4′-methoxythioaurone 3b.
