71094-28-5

Upstream product

• 532-27-4 1-chloroacetophenone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-86-2 acetophenone 

Downstream Products

• 41780-81-8 1-phenyl-1-butanone 2-naphthylethanone p-toluenesulfonylhydrazone 
• 1217009-30-7 4-methyl-N'-(3,3-dimethyl-1-phenylbutylidene)benzenesulfonohydrazide 
• 72770-60-6 4-methyl-N'-(3-methyl-1-phenylbutylidene)benzenesulfonohydrazide 
• 13148-78-2 1,4-diphenyl-[1,2,3]-triazole 
• 634604-04-9 4-phenyl-1-(p-tolyl)-1H-1,2,3-triazole 
• 116373-83-2 1‐(4‐bromophenyl)‐4‐phenyl‐1H‐1,2,3‐triazole 
• 1268461-16-0 ethyl-4-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoate 
• 1381887-02-0 1-(naphthalene-2-yl)-4-phenyl-1H-1,2,3-triazole 
• 1258783-13-9 1-(2-bromophenyl)-4-phenyl-1H-1,2,3-triazole 
• 2101-57-7 1-(4-nitrophenyl)-4-phenyl-1H-1,2,3-triazole 
• 25445-77-6 4-phenyl-1,2,3-thiadiazole 

Relevant academic research and scientific papers

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.

Cascade Trisulfur Radical Anion (S3?-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles

Trisulfur radical anion (S3?-) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3?- is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C-S and N-S bonds via S3?- addition and electron detosylation under mild conditions.

Aerobic Oxidative Cycloaddition of α-Chlorotosylhydrazones with Arylamines: General Chemoselective Construction of 1,4-Disubstituted and 1,5-Disubstituted 1,2,3-Triazoles under Metal-Free and Azide-Free Conditions

A novel synthetic approach toward 1,4-disubstituted 1,2,3-triazoles and 1,5-disubstituted 1,2,3-triazoles by aerobic oxidative cycloaddition of α-chlorotosylhydrazone with primary aryl amine has been developed. Significantly, the reaction proceeds smoothl

Copper-catalyzed enantioselective inverse electron-demand hetero-diels-alder reactions of diazadienes with enol ethers: Efficient synthesis of chiral pyridazines

A highly efficient and enantioselective inverse electron-demand hetero-Diels-Alder reaction of in situ generated 1,2-diaza-1,3-dienes with enol ethers has been developed with the use of a chiral copper/bisoxazoline complex as the catalyst. The reaction ex

Copper(I)-catalyzed addition of grignard reagents to in situ-derived N -sulfonyl azoalkenes: An umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers

The α-alkylation of N-sulfonyl hydrazones via in situ-derived azoalkenes provides an umpolung approach to ketone α-alkylation that has considerable potential with regard to catalysis and the direct incorporation of functionality not amenable to the use of enolate chemistry. Herein, we describe the first Cu(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes. This method is remarkable in its ability to deliver highly sterically hindered compounds that would be difficult or impossible to synthesize via traditional enolate chemistry, including those having up to three contiguous quaternary centers.

Conversion of Tosylhydrazones of α-Halogeno-aldehydes and -ketones into the Corresponding Phenylthio- and Phenylseleno-derivatives

The tosylhydrazones of 2-chlorocyclohexanone, 2-chlorocyclopentanone, 1-chloropropanone, phenacyl chloride, 2-bromoheptanal and 2-bromo-2-methylpropanal (1), (5a),(7a),(8b), and (9b), respectively, reacted rapidly with thiophenol and an excess of triethylamine in tetrahydrofuran at -78 deg C to give the corresponding α-phenylthio-substituted tosylhydrazones (3a), (5b), (7b), (8c), and (9c) in good yields.The α-phenylseleno-substituted tosylhydrazones (3b),(5c), (6c), (8d), and (9d) were similarly prepared, in satisfactory yields, by treating the corresponding α-halogeno-substituted tosylhydrazones with benzeneselenol and an excess of triethylamine.Several α-phenylthio-substituted carbonyl compounds and 2-phenylselenocyclohexanone (4b) were regenerated from the corresponding tosylhydrazones in good yields.