158918-49-1

Upstream product

• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 13397-96-1 1-bromo-2-pentylbenzene 
• 78348-98-8 1-(2-bromophenyl)pentan-1-ol 
• 56667-12-0 (Z)-2,2'-dibromostilbene 
• 136859-33-1 1-bromo-2-(4-tolylsulfonylmethyl)benzene 
• 18982-54-2 o-bromobenzyl alcohol 
• 63646-32-2 C₁₈H₁₂BrNO 
• 1387637-91-3 5-(2-bromophenyl)-3-phenyl-1H-pyrazole 
• 1454253-91-8 5-(o-bromophenyl)-4-phenyl-1H-pyrazole 
• 1454253-87-2 C₁₃H₉BrN₂O 
• 1454253-88-3 C₁₆H₁₃BrN₂ 
• 1454253-89-4 C₁₄H₁₁BrN₂O 
• 1383470-42-5 C₁₁H₁₁BrN₂ 
• 1454769-92-6 (E)-1,3-dimethyl-3-(2'-bromostyryl)indolin-2-one 
• 23300-99-4 1-tosyl-1H-indazole 

Relevant academic research and scientific papers

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

Acid-Promoted [3 + 1 + 1] Cyclization of N-Tosylhydrazones and Isocyanides: A Method for the Preparation of 4,5-Diaminopyrazoles

A facile method for the preparation of 4,5-diaminopyrazoles from N-tosylhydrazones and isocyanides was developed. The reaction was general for a wide range of substrates, and it demonstrated excellent tolerance to a variety of substituents. More important

Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.

Copper-catalyzed cross-coupling and sequential allene-mediated cyclization for the synthesis of 1,2,3-triazolo[1,5-a]quinolines

In this paper, a tandem reaction involving copper-catalyzed cross-coupling and allene-mediated cyclization of 1-(2-ethynylaryl)-1,4-disubstituted-1,2,3-triazole withN-tosylhydrazone has been developed. This method features operational simplicity, excellen

Ring-Opening of Indoles: An Unconventional Route for the Transformation of Indoles to 1 H-Pyrazoles Using Lewis Acid

An unusual transformation of indoles to pyrazoles via an aromatic ring-opening strategy has been developed. The salient feature of this strategy involves the C2-N1 bond opening and concomitant cyclization reaction of the C2=C3 bond of the indole moiety with the tosylhydrazone, which proceeds under transition-metal and ligand free conditions. This ring-opening functionalization of indoles provides a wide scope of differently substituted pyrazoles.

Base-Promoted Denitrogenative/Deoxygenative/Deformylative Benzannulation of N-Tosylhydrazones with 3-Formylchromones for Diverse and Polyfunctionalized Xanthones

A simple and efficient base-promoted denitrogenative/deoxygenative/deformylative benzannulation is developed for the construction of biologically interesting polyfunctionalized xanthones starting from N-tosylhydrazones and two molecules of 3-formylchromon

Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N-tosylhydrazones under metal-free conditions

A metal-free cyclopropanation of electron-deficient olefins 3-substituted-2-cyanoacrylamides with N-tosylhydrazones has been successfully developed. This strategy provide a simple route to the synthesis of very valuable 1-cyanocyclopropanecarboxamides wit

Multi-component one-pot reaction of aromatic carbonyl compounds, tosylhydrazide, and arylboronic acids

In this paper, we developed a new method using 4-bromoacetophenone as the starting material, with tosylhydrazide and two arylboronic acids using Barluenga and Suzuki couplings in a four-component one-pot reaction to afford the target product 4-benzyl-1,1-biphenyls. This system that we have developed enables the use of easily accessible starting materials and can be employed on a wide variety of substrates with good functional group tolerance. In particular, this protocol can be applied to the synthesis of 4-(1-([1,1-biphenyl]-4-yl)ethyl)pyridine derivatives, a class of potential analogs of CPY17 inhibitors of prostate cancer.

Metal-Free Ring-Expansion Reaction of Six-membered Sulfonylimines with Diazomethanes: An Approach toward Seven-Membered Enesulfonamides

A new metal-free, ring-expansion reaction of six-membered N-sulfonylimines with unstable diazomethanes, generated in situ from the N-tosylhydrazones, has been developed. This reaction delivers valuable seven-membered enesulfonamides by a Tiffeneau-Demjanov rearrangement and intramolecular proton transfer tautomerization process. Moreover, this ring-expansion reaction can be carried out in a one-pot fashion and scaled up to the gram scale by using aryl aldehydes, without the need to isolate the N-tosylhydrazone. A diazo thing: The title reaction between cyclic N-sulfonylimines and diazo compounds generated in situ from the N-tosylhydrazones is simple and functional-group tolerant. It thus delivers valuable seven-membered sulfonamides in up to 95 % yield. Moreover, this reaction can be carried out in one-pot starting from the aryl aldehydes, without the need to isolate the N-tosylhydrazone (right).

Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.