3051-27-2

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 5219, 1950 DOI: 10.1021/ja01167a120

InChI:InChI=1/C8H8O2S/c1-6(9)5-7(10)8-3-2-4-11-8/h2-4H,5H2,1H3

Upstream product

• 3437-95-4 2-Iodothiophene 
• 201230-82-2 carbon monoxide 
• 67-64-1 acetone 
• 874-83-9 (E)-4-(2-thienyl)but-3-en-2-one 
• 98-03-3 thiophene-2-carbaldehyde 
• 62889-07-0 trimethyl((1-(thiophen-2-yl)vinyl)oxy)silane 
• 88-15-3 2-Acetylthiophene 
• 2810-04-0 Ethyl thiophene-2-carboxylate 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 100621-03-2 3-methyl-1-phenyl-5-[2]thienyl-1H-pyrazole 
• 100541-56-8 3-methyl-1-(4-nitro-phenyl)-5-[2]thienyl-1H-pyrazole 
• 31618-80-1 3-methyl-5-thiophen-2yl-1-hydropyrazole 
• 31894-56-1 Ethyl-2methyl-4(2thienyl)-5pyrrole carboxylate 
• 26963-43-9 2-Amino-4-methyl-6-thien-2-yl-pyrimidin 
• 128228-80-8 4-(4-Chloro-phenyl)-2-(3-methyl-5-thiophen-2-yl-pyrazol-1-yl)-thiazole 
• 128228-79-5 2-<3-methyl-5-(2-thienyl)pyrazol-1-yl>-4-phenylthiazole 
• 127144-08-5 4-Methyl-6-(2-thienyl)-2-thioxo-1,2-dihydro-pyridin-3-carbonitril 
• 127144-09-6 6-Methyl-4-(2-thienyl)-2-thioxo-1,2-dihydro-pyridin-3-carbonitril 
• 128228-82-0 2-(3-Methyl-5-thiophen-2-yl-pyrazol-1-yl)-4-(4-nitro-phenyl)-thiazole 
• 96723-33-0 1-(4-methylphenyl)-3-carbomethoxy-4-(2-thenoyl)-5-methylpyrazole 
• 127144-10-9 2-Ethoxycarbonylmethylthio-4-methyl-6-(2-thienyl)-pyridin-3-carbonitril 
• 127144-11-0 2-Ethoxycarbonylmethylthio-6-methyl-4-(2-thienyl)-pyridin-3-carbonitril 
• 128228-88-6 6-Chloro-2-(3-methyl-5-thiophen-2-yl-pyrazol-1-yl)-benzothiazole 

Relevant academic research and scientific papers

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

A versatile and robust synthetic protocol for the preparation of β-diketones bearing 2-thienyl and perfluorinated alkyl radicals of different length or a methyl group was developed. This protocol is suitable for the preparation of multigram quantities of diketones without cumbersome purification procedures. Moreover, the known method for purification of diketones via copper chelates was improved considerably.

Discovery of pyrazole N-aryl sulfonate: A novel and highly potent cyclooxygenase-2 (COX-2) selective inhibitors

Based on a new pyrazole sulfonate synthetic method, a novel class of molecules with a basic structure of pyrazole N-aryl sulfonate have been designed and synthesized. The interest in conducting intensive research stems from quite evident anti-inflammatory effects exhibited by the compounds in preliminary animal experiments. A series of compounds were synthesized by different substitutions of the R1, R2, and R3 groups. Within the series, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and phenyl 5-methyl-3-(4-(trifluoromethyl) phenyl)-1H-pyrazole-1-sulfonate exhibited excellent anti-inflammatory activity (% inhibition of auricular edemas = 27.0 and 35.9, respectively); the in vivo analgesic activity of phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate was confirmed to be effective (inhibition ratio of writhing = 50.7% and 48.5% separately), and compounds phenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate, 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate were identified as selective COX-2 inhibitors (SI = 455, 10,497 and >189 severally). In Acute Oral Toxicity assays conducted in vivo, the lethal dose 50 (LD50) of 4-iodophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate and 2-chlorophenyl 5-methyl-3-(p-tolyl)-1H-pyrazole-1-sulfonate to mice was >2000 mg/kg BW.

Direct synthesis of 2,3,5-trisubstituted pyrroles: via copper-mediated one-pot multicomponent reaction

We have developed a copper-mediated one-pot synthesis of 2,3,5-trisubstituted pyrroles from 1,3-dicarbonyl compounds and acrylates using ammonium acetate as a nitrogen source. The reaction achieves C-C and C-N bond formation and provides an efficient approach to access highly functionalized pyrroles without further raw material preparation. This method is operationally simple, compatible with a wide range of functional groups, and provides the target products in moderate to good yields. This journal is

Direct Access to Functionalized Indoles via Single Electron Oxidation Induced Coupling of Diarylamines with 1,3-Dicarbonyl Compounds

Under aerobic copper catalysis, an unprecedented direct synthesis of functionalized indoles via single electron oxidation induced coupling of diarylamines with 1,3-dicarbonyl compounds is presented. The protocol proceeds with good functional group and substrate compatibility, the use of readily available feedstocks and naturally abundant catalyst system, high step and atom efficiency, as well as selectivity, which offers a platform for accessing a new class of indoles with the potential for the discovery of functional molecules.

Pyrrolecarboxylic acid derivative synthesis method

The invention discloses a pyrrolecarboxylic acid derivative synthesis method, which comprises: obtaining a group substituted formylacetone derivative by using a group substituted acetyl derivative andethyl acetate as raw materials; carrying out cyclization with diethyl aminomalonate hydrochloride to generate a pyrrolecarboxylic acid derivative ethyl ester; and carrying out a hydrolysis reaction to obtain the target product pyrrolecarboxylic acid derivative. According to the present invention, the method has characteristics of mild reaction conditions, simple purification, high yield and highproduct purity, and is suitable for process amplification and mass production.

Determination of the enol form of asymmetric 1,3-dicarbonyl compounds: 2D HMBC NMR data and DFT calculations

In this study, a series of asymmetric aryl 1,3-dicarbonyl compounds were synthesized and their enol forms were observed via experimental data and theoretical calculations. According to the 1H-and 13C-NMR results, all the investigated compounds were found

Discovery and structure-activity relationships study of thieno[2,3-b]pyridine analogues as hepatic gluconeogenesis inhibitors

Type 2 diabetes mellitus (T2DM) is a chronic, complex and multifactorial metabolic disorder, and targeting gluconeogenesis inhibition is a promising strategy for anti-diabetic drug discovery. This study discovered a new class of thieno[2,3-b]pyridine derivatives as hepatic gluconeogenesis inhibitors. First, a hit compound (DMT: IC50 = 33.8 μM) characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. Structure activity relationships (SARs) study showed that replaced the CF3 in the thienopyridine core could improve the potency and led to the discovery of 8e (IC50 = 16.8 μM) and 9d (IC50 = 12.3 μM) with potent inhibition of hepatic glucose production and good drug-like properties. Furthermore, the mechanism of 8e for the inhibition of hepatic glucose production was also identified, which could be effective through the reductive expression of the mRNA transcription level of gluconeogenic genes, including glucose-6-phosphatase (G6Pase) and hepatic phosphoenolpyruvate carboxykinase (PEPCK). Additionally, 8e could also reduce the fasting blood glucose and improve the oral glucose tolerance and pyruvate tolerance in db/db mice. The optimization of this class of derivatives had provided us a start point to develop new anti-hepatic gluconeogenesis agents.

Pyrazole compound containing N-aryl sulfonate and synthesis and application thereof

The invention discloses a pyrazole compound containing N-aryl sulfonate. A structural formula of the pyrazole compound is shown in the description. Proofed by pharmacological study, the pyrazole compound has the advantages that the activity of cyclooxygenase 2 is inhibited; the high-efficiency inhibition function on the generation of cyclooxygenase 2 due to inflammation mediums is realized, so that the pyrazole compound can be used as an active matter, and the prepared anti-inflammation medicine can be used for treating the inflammations, such as rheumatic arthritis and rheumatalgia, and the diseases and symptoms, such as fevers.

Rhodium(ii)-catalysed generation of cycloprop-1-en-1-yl ketones and their rearrangement to 5-aryl-2-siloxyfurans

Donor-acceptor cyclopropenes formed from enoldiazoketones undergo catalytic rearrangement to 5-aryl-2-siloxyfurans via a novel mechanism that involves a nucleophilic addition of the carbonyl oxygen to the rhodium-activated cyclopropene.

Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules

A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.