14062-05-6

Usage

Uses

Used in Organic Synthesis:
1,2-Bis(p-tolylsulfonyl)hydrazine, N,Nμ-Ditosylhydrazine, and 4-Methylbenzenesulfonic acid 2-[(4-methylphenyl)sulfonyl]hydrazide are used as reagents in organic synthesis for their ability to facilitate various chemical reactions. They are particularly useful in the preparation of polymeric and organic compounds due to their unique properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, these hydrazine derivatives are used as intermediates in the synthesis of various drugs and pharmaceutical compounds. Their unique chemical structures and reactivity make them valuable in the development of new therapeutic agents.
Used in Chemical Research:
1,2-Bis(p-tolylsulfonyl)hydrazine, N,Nμ-Ditosylhydrazine, and 4-Methylbenzenesulfonic acid 2-[(4-methylphenyl)sulfonyl]hydrazide are also used in chemical research to explore their properties and potential applications. Researchers utilize these compounds to study reaction mechanisms, develop new synthetic methods, and discover novel compounds with potential applications in various fields.
Used in Material Science:
In the field of material science, these hydrazine derivatives are employed in the synthesis of advanced materials with specific properties. Their unique chemical structures allow them to be incorporated into the development of new materials with potential applications in various industries, such as electronics, energy, and nanotechnology.

InChI:InChI=1/C14H16N2O4S2/c1-11-3-7-13(8-4-11)21(17,18)15-16-22(19,20)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3

Upstream product

• 120-46-7 1,3-diphenylpropanedione 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 123-54-6 acetylacetone 
• 104-15-4 toluene-4-sulfonic acid 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 171007-71-9 3-phenyl-1-propyl diazoacetate 
• 1212022-63-3 C₂₆H₂₆N₂O₆S₂ 
• 1360762-44-2 (3R,5R)-5-ethyl-1,2-bis(p-toluenesulfonyl)pyrazolidin-3-ol 
• 1360762-47-5 (5R)-5-ethyl-1,2-bis(p-toluenesulfonyl)pyrazolidine 
• 1360762-45-3 (3R,5R)-5-butyl-1,2-bis(p-toluenesulfonyl)pyrazolidin-3-ol 
• 1360762-48-6 (5R)-5-butyl-1,2-bis(p-toluenesulfonyl)pyrazolidine 
• 1360467-58-8 4-methylbenzenesulfinic acid 1,1,3,3-tetramethylguanidine salt 
• 95205-14-4 α-diazo-N,N-tetramethyleneacetamide 
• 24761-87-3 2-diazo-1-(piperidin-1-yl)ethan-1-one 
• 881771-93-3 1-(piperidin-1-yl)-2-(p-tosyl)ethan-1-one 
• 172698-60-1 1-(azepan-1-yl)-2-diazoethanone 
• 1289636-05-0 tert-butyl 4-(2-diazoacetyl)piperazine-1-carboxylate 
• 1342316-11-3 2-diazo-1-(1,1-dioxido-4-thiomorpholinyl)ethanone 

Relevant academic research and scientific papers

A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938

Chiral Br?nsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

One-step synthesis of cyclic polypyrazole and the self-assembly vesicles driven by hydrogen bond

The synthesis of cyclic polymer is an important topic in polymer chemistry. Herein, we report a one-step method to prepare cyclic polypyrazoles. Monomers with two functional groups, diazo and alkyne, were synthesized and polymerized via 1,3-diploar cycloa

Fast Living Polymerization and Helix-Sense-Selective Polymerization of Diazoacetates Using Air-Stable Palladium(II) Catalysts

In this work, air-stable palladium(II) catalysts bearing bidentate phosphine ligands were designed and prepared, which could initiate fast and living polymerizations of various diazoacetate monomers under mild conditions. The polymerization afforded the desired polymers in high yields with controlled molecular weights (Mns) and narrow molecular weight distributions (Mw/Mns). The Mns of the isolated polymers were linearly correlated to the initial feed ratios of monomer to catalyst, confirming the living/controlled manner of the polymerizations. The Mn also increased linearly with the monomer conversion, and all of the isolated polymers showed narrow Mw/Mns. The polymerization was relatively fast and could be accomplished within several minutes. Such fast living polymerization method can be applied to a wide range of diazoacetate monomers in various organic solvents at room temperature in air. Taking advantage of the living nature, we facilely prepared a series of block copolymers through chain extension reactions. The amphiphilic block copolymers synthesized by this method exhibited interesting self-assembly properties. Moreover, polymerization of achiral bulky diazoacetate by Pd(II) catalysts bearing a chiral bidentate phosphine ligand leads to the formation of polymers with high optical activity due to the formation of the predominantly one-handed helix of the main chain. The helix sense of the polymers was determined by the chirality of the Pd(II) catalysts.

Asymmetric transfer hydrogenation of heterocycle-containing acetophenone derivatives using N-functionalised [(benzene)Ru(II)(TsDPEN)] complexes

The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of α-heterocyclic acetophenone derivatives is reported. Products of up to 99% ee were formed.

ALCOHOL DERIVATIVES AS KV7 POTASSIUM CHANNEL OPENERS

The present invention provides novel compounds which activate the Kv7 potassium channels. Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds to treat disorders responsive to the activation of Kv7 potassium channels.

Synthesis of 4-substituted-3-Hydroxyquinolin-2(1H)-ones with anticancer activity

Herein we show that the 3-hydroxyquinolin-2(1H)-one (3HQ) core is a suitable platform to develop new compounds with anticancer activity against MCF-7 (IC50 up to 4.82 μM) and NCI–H460 (IC50 up to 1.8 μM) cancer cell lines. The ring-expansion reaction of isatins with diazo esters catalysed by di-rhodium (II) complexes proved to be a simple and effective strategy to synthesize 4-carboxylate-3HQs (yields up to 92%). 4-Carboxamide-3HQs were more efficiently prepared using NHS-diazoacetate in yields up to 88%. This innovative methodology enabled the construction of “peptidic-like” 3HQs, with several amino acid substituents. Among this series, the L-leucine derivative induced the cell death of MCF-7 (IC50 of 15.1 μM) and NCI–H460 (IC50 of 2.7 μM) cancer cell lines without causing any appreciable cytotoxicity against the non-cancer cell model (CHOK1).

A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938

Chiral Br?nsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of (S)-PD 172938 has been demonstrated by using this protocol.

Synthesis of α-aminocarbonyl compounds via hetero dielsalder reaction

A synthetic route to α-aminoketone derivatives via a hetero DielsAlder reaction is described. Diacylhydrazine was oxidized by tert-butyl hypochlorite in the presence of pyridine. After evaporation, the hetero DielsAlder reaction with diene was carried out without isolation of the azodicarbonyl compound. Quantitative hetero DielsAlder reaction was possible with 1 equivalent of diene when Hf(OTf)4 or AgOTf was used as the catalyst. The NN bond of the product was cleaved by SmI2-reduction in the presence of tert-BuOH in THF. Further, ozonolysis of the C=C double bond afforded the α-aminoketone derivative in excellent yield.

A chiral Br?nsted acid-catalyzed highly enantioselective Mannich-type reaction of α-diazo esters with in situ generated N -acyl ketimines

A chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction of α-diazo esters with in situ generated N-acyl ketimines, derived from 3-hydroxyisoindolinones has been demonstrated in this communication. A variety of isoindolinone-based α-amino diazo esters bearing a quaternary stereogenic center were afforded in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the products has been depicted by the hydrogenation of the diazo moiety of adducts.

Synthesis of C-Unsubstituted 1,2-Diazetidines and Their Ring-Opening Reactions via Selective N-N Bond Cleavage

C-Unsubstituted 1,2-diazetidines, a rarely studied type of four-membered heterocyclic compounds, were synthesized through an operationally simple intermolecular vicinal disubstitution reaction. 1,2-Diazetidine derivatives bearing various N-arylsulfonyl groups were readily accessed and studied by experimental and computed Raman spectra. The ring-opening reaction of the diazetidine was explored and resulted in the identification of a selective N-N bond cleavage with thiols as nucleophiles, which stereoselectively produced a new class of N-sulfenylimine derivatives with C-aminomethyl groups.