3139-42-2

Usage

Uses

Used in Organic Synthesis:
(2Z)-2-benzylidene-1-benzothiophen-3(2H)-one is utilized as an intermediate in organic synthesis for the development of various chemical compounds. Its unique structure allows it to participate in multiple chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, (2Z)-2-benzylidene-1-benzothiophen-3(2H)-one is used as a key building block for the creation of new drug candidates. Its potential pharmacological properties, such as anti-inflammatory and antimicrobial activities, make it a promising candidate for the development of novel therapeutic agents to treat various diseases and conditions.
Used in Chemical Reactions:
(2Z)-2-benzylidene-1-benzothiophen-3(2H)-one is employed as a reactant in various chemical reactions, enabling the formation of new compounds with diverse applications. Its reactivity and structural features contribute to the synthesis of complex organic molecules, which can be further utilized in different industries, including materials science and specialty chemicals.

Upstream product

• 108-98-5 thiophenol 
• 130-03-0 thioindoxyl 
• 100-52-7 benzaldehyde 
• 103-04-8 (phenylthio)acetic acid 
• 7031-27-8 (phenylthio)acetic acid chloride 
• 63329-72-6 (Z)-2-benzylidenebenzo[b]thiophen-3(2H)-one 
• 117968-43-1 (Z)-2-Methanesulfinyl-1-[2-(4-methoxy-benzylsulfanyl)-phenyl]-3-phenyl-propenone 
• 62786-15-6 2-benzylidene-1-benzothiophen-3(2H)-one 
• 58109-92-5 2-phenylthiochroman-4-one 1-oxide 
• 16619-38-8 2'-nitro-chalcone 
• 32784-07-9 3-bromo-2-phenyl-thiochroman-4-one 
• 493-57-2 benzo-[b]thiophene-2,3-dione 
• 147-93-3 Thiosalicylic acid 
• 1531-80-2 2-(benzylthio)benzoic acid 

Relevant academic research and scientific papers

Asymmetric (4 + 3) and (4 + 1) Annulations of Isatin-derived Morita-Baylis-Hillman Carbonates to Construct Diverse Chiral Heterocyclic Frameworks

A chiral tertiary amine-catalyzed asymmetric γ-regioselective (4 + 3) annulation reaction of isatin-derived Morita-Baylis-Hillman carbonates and 1-azadienes was developed, delivering chiral azepane spirooxindoles with excellent stereoselectivity. In addition, by tuning the substituents of Morita-Baylis-Hillman carbonates, the switchable γ-(4 + 3) or α-(4 + 1) annulation reaction with o-quinone methides was observed to furnish benzo[b]oxepines or 2,3-dihydrobenzofurans, respectively, under similar catalytic conditions.

Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction

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

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

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

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

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.

Making fast photoswitches faster - Using hammett analysis to understand the limit of donor-acceptor approaches for faster hemithioindigo photoswitches

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

Iodine-catalyzed intramolecular oxidative thiolation of vinylic carbon-hydrogen bonds via tandem iodocyclization and dehydroiodination: Construction of 2-methylene-3-thiophenones

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.

One-step synthesis of thioaurones

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.