93876-77-8

Upstream product

• 4661-46-5 2-carboxybenzene diazonium chloride 
• 100989-99-9 3,4-Di-p-tolyl-2,5-dihydro-thiophene 
• 100990-22-5 (3R,4S)-3,4-Di-p-tolyl-tetrahydro-thiophene-3,4-diol 
• 23080-22-0 bis(2-(4-methylphenyl)ethanonyl)sulfide 
• 3141-26-2 3,4-dibromothiophene 
• 5720-05-8 4-methylphenylboronic acid 
• 3457-48-5 1,2-di(4-methylphenyl)-1,2-ethanedione 

Downstream Products

• 854625-95-9 3,4-di-p-tolyl-thiophene-1,1-dioxide 
• 951384-60-4 C₄SBr₂(C₆H₄CH₃)2 
• 1351662-68-4 3,3',4,4'-tetra(p-tolyl)-2,2'-bithiophene 
• 102402-61-9 3,4-di-p-tolyl-2,5-dihydro-thiophene-1,1-dioxide 

Relevant academic research and scientific papers

Straightforward Synthesis, Electrochemical Properties, and Gel Formation of Thiacalix[n]thiophenes

A facile synthetic approach toward thiacalix[n]thiophene homologues (n=4-6) is presented herein. Pd-catalyzed coupling of 2,5-dibromothiophene derivatives with stannyl sulfide gave various thiacalix[n]thiophenes in good yields. The optical and electrochem

Identification and structure-activity relationships of a novel series of estrogen receptor ligands based on 7-thiabicyclo[2.2.1]hept-2-ene-7-oxide

To develop estrogen receptor (ER) ligands having novel structures and activities, we have explored compounds in which the central hydrophobic core has a more three-dimensional topology than typically found in estrogen ligands and thus exploits the unfilled space in the ligand-binding pocket. Here, we build upon our previous investigations of 7-oxabicyclo[2.2.1]heptene core ligands, by replacing the oxygen bridge with a sulfoxide. These new 7-thiabicyclo[2.2.1] hept-2-ene-7-oxides were conveniently prepared by a Diels-Alder reaction of 3,4-diarylthiophenes with dienophiles in the presence of an oxidant and give cycloadducts with endo stereochemistry. Several new compounds demonstrated high binding affinities with excellent ERα selectivity, but unlike oxabicyclic compounds, which are transcriptional antagonists, most thiabicyclic compounds are potent, ERα-selective agonists. Modeling suggests that the gain in activity of the thiabicyclic compounds arises from their endo stereochemistry that stabilizes an active ER conformation. Further, the disposition of methyl substituents in the phenyl groups attached to the bicyclic core unit contributes to their binding affinity and subtype selectivity.

Oxidation of 3,4-diaryl-2,5-dihydrothiophenes to 3,4-diarylthiophenes using CuBr2: Simple and efficient preparation of 3,4-diarylthiophenes

A class of 3,4-diarylthiophenes was prepared in excellent yield (80-91%) by oxidation of 3,4-diaryl-2,5-dihydrothiophenes with CuBr2. The approach is also available for the synthesis of 3,4-diarylpyrroles and 3,4-diarylfuran. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

PREPARATION OF 1-PHENYLTHIO-1,3-DIENES BY REACTION OF 2,5-DIHYDROTHIOPHENES WITH BENZYNE THROUGH FRAGMENTATION OF SULFONIUM YLIDE INTERMEDIATES

The reaction of a series of 2,5-dihydrothiophenes with benzyne, generated from 2-carboxybenzenediazonium chloride, affords 1-phenylthio-1,3-dienes in good yields through the fragmentation of sulfonium ylide intermediates.

GENERAL SYNTHESIS OF 2,5-DIHYDROTHIOPHENES (3-THIOLENES) FROM DIKETO SULFIDES

The intramolecular reductive coupling reaction of easily accesible diketo sulfides by a low-valent titanium reagent (prepared from titanium(IV) chloride and zinc powder) provides an efficient general synthesis of 2,5-dihydrothiophenes.

GENERAL SYNTHESIS OF POLYSUBSTITUTED THIOPHENES FROM DIKETO SULFIDES

Treatment of diketo sulfides with a low-valent titanium reagent at 0 deg C (in two cases at room temperature) affords 3,4-dihydroxythiolanes in good yields.The acid-catalyzed (p-toluenesulfonic acid) dehydration of the latter compounds leads to the corres