25746-67-2

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 10, p. 5, 1973 DOI: 10.1002/jhet.5570100102

Upstream product

• 98-86-2 acetophenone 
• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 70-11-1 α-bromoacetophenone 
• 82229-60-5 1-Phenyl-2-phenylsulfanyl-2-(1-phenyl-1H-tetrazol-5-ylsulfanyl)-ethanone 

Downstream Products

• 1174193-91-9 C₂₀H₂₀N₄O₄S 
• 1394140-03-4 5-[4-phenyl-1,2,3-selenadiazol-5-yl]sulfanyl-1-phenyl-1H-1,2,3,4-tetraazole 
• 1338710-68-1 2,4-diphenyl-3-[(1-phenyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]quinoline 

Relevant academic research and scientific papers

A DEVELOPING AGENT PRECURSOR FOR LASER MARKABLE COMPOSITIONS

The invention relates to novel laser markable compositions comprising developing agent precursors according to formula (I).

Preparation method of alpha-heterocycle sulfide ketone compound

The invention provides a method for efficiently synthesizing different heterocycle sulfide ketone derivatives. According to the method, KI is adopted as a catalyst, potassium persulfate is adopted as an oxidizing agent, a carbonyl compound and benzoheterocycle mercaptan are taken as reaction substrates at room temperature, and DMSO is added into a reaction system as a solvent. The method provided by the invention has the advantages that the catalyst is cheap and available; reaction conditions are mild, and reaction can be carried out at room temperature, thereby being safe and reliable; and the highest yield of the obtained target product reaches 94%. The method provided by the invention overcomes the defects that a substrate of the traditional heterocycle thio etherification reaction is expensive, multi-step reaction is required to be carried out and reaction conditions are harsh, and the method provided by the invention has a good industrial application prospect.

KI/K 2 S 2 O 8 -Mediated α-C-H Sulfenylation of Carbonyl Compounds with (Hetero)Aryl Thiols

A new and facile KI/K 2 S 2 O 8 -mediated α-C-H sulfenylation of carbonyl compounds with (hetero)aryl thiols was developed for the formation of C-S bond at room temperature. This method provided a simple process for the sy

Iodine Promoted Regioselective α-Sulfenylation of Carbonyl Compounds using Dimethyl Sulfoxide as an Oxidant

A metal-free regioselective sulfenylation of the α-CH3 group of ketones has been achieved in the presence of the α-CH2 or α-CH group using the cross dehydrogenative (CDC) strategy. Aldehydes also exhibit good selectivity forming the corresponding α-sulfenylated products. This efficient sulfenylation of ketones or aldehydes with thiones or heterocyclic thiols utilizes dimethyl sulfoxide (DMSO) as an oxidant in the presence of iodine. This eco-friendly method uses readily available and inexpensive I2 and DMSO. The application of this methodology has been demonstrated by synthesizing precursors for Julia- Kocienski olefination intermediates.

Synthesis and characterization of 5-heteroarylsulfanyl-4-aryl- 1,2,3-selena/thiadiazoles

Synthesis and spectral characterization of 2-methyl-5-[(4-aryl-1,2,3- selenadiazol-5-yl)sulfanyl]-1,3,4-thiadiazoles, 5-[4-aryl-1,2,3-selenadiazol-5- yl]sulfanyl-1-phenyl-1H-1,2,3,4-tetraazoles, 4-aryl-5-[(5-methyl-1,3,4- thiadiazol-2-yl)sulfanyl]-1,2,3-t

Practical synthesis of β-carbonyl phenyltetrazolesulfones and investigations of their reactivities in organocatalysis

A practical synthesis of β-carbonyl phenyltetrazolesulfones, useful for a series of enantioselective reactions, is shown. Aryl, alkyl and ester carbonyl compounds all proved to be efficiently synthesised, leading to products in up to >99% yield over two s

Modulation of 11β-hydroxysteroid dehydrogenase type 1 activity by 1,5-substituted 1H-tetrazoles

Inhibitors of 11β-hydroxysteroid dehydrogenase (11β-HSD1) show promise as drugs to treat metabolic disease and CNS disorders such as cognitive impairment. A series of 1,5-substituted 1H-tetrazole 11β-HSD1 inhibitors has been discovered and chemically modified. Compounds are selective for 11β-HSD1 over 11β-HSD2 and possess good cellular potency in human and murine 11β-HSD1 assays. A range of in vitro stabilities are observed in human liver microsome assays.

Synthesis of chalcones and flavanones using Julia-Kocienski olefination

A new application of Julia-Kocienski olefination for the synthesis of chalcones and flavanones has been described. 2-(Benzo[d]thiazol-2-ylsulfonyl)-1- phenylethanones have been developed as new reagents for direct Julia-Kocienski olefination with aldehydes in the presence of a base, afforded chalcones in good to excellent yields. Whereas, 2-(benzo[d]thiazol-2-ylsulfonyl)-1-(2- hydroxyphenyl)ethanone reacted with the aromatic aldehydes to furnish flavanones in good yields via one-pot intra-molecular cyclization.

Asymmetric organocatalytic formal alkynylation and alkenylation of α,β-unsaturated aldehydes

A highly stereoselective organocatalytic one-pot protocol for the formal alkynylation and alkenylation of α,β-unsaturated aldehydes using novel chemistry based on β-keto heterocyclic sulfones is presented. The organocatalytic step is catalyzed by a prolinol derivative and allows for the formation of important optically active compounds. Further transformations of the β-keto heterocyclic sulfone moiety, based on new developments of the Smiles rearrangement through a process parallel to the Julia-Kocienski reaction, were performed leading to β-alkynylated aldehydes and 3-alkenylated alcohols. The scopes of both transformations are demonstrated by the synthesis of various optically active alkynes and alkenes. Furthermore, different transformations of the aldehyde and the alcohol functionality were performed. Finally, the proposed mechanisms for both the alkynylation and alkenylation of α,β-unsaturated aldehydes are outlined.

1,5-SUBSTITUTED TETRAZOLES AS THERAPEUTIC COMPOUNDS

The present invention pertains to certain 1,5-substituted-1H-tetrazole compounds that, inter alia, inhibit 11β- hydroxysteroid dehydrogenase type 1 (11β-HSD1). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, bothin vitro and in vivo, to inhibit 11β-hydroxysteroid dehydrogenase type 1; to treat conditions that are ameliorated by the inhibition of 11β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes conditions such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS conditions such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc.