Sulfonyl Hydrazides Research Articles

ChemInform Abstract: Iodine‐Catalyzed Three‐Component Oxysulfenylation of Alkenes with Sulfonyl Hydrazides and Alcohols.

AbstractThe three‐component oxysulfenylation fails with acyclic 1,2‐disubstituted alkenes such as (E)‐stilbene and 2‐methyl‐1‐phenyl‐1‐propene.

ChemInform Abstract: Convenient MW‐Assisted Synthesis of Unsymmetrical Sulfides Using Sulfonyl Hydrazides as Aryl Thiol Surrogate.

An efficient synthesis of unsymmetrical sulfides has been achieved via the cross-coupling reaction of aryl/het-aryl/benzyl halides with stable and easily workable sulfonyl hydrazides as thiol substitutes by means of [DBU][HOAc] and CuI under microwave irradiation.

Iodine-catalyzed three-component oxysulfenylation of alkenes with sulfonyl hydrazides and alcohols

An unprecedented three-component oxysulfenylation reaction of alkenes with sulfonyl hydrazides and alcohols has been developed in the presence of 20 mol% iodine to give a range of structurally diverse β-alkoxy sulfides in good to excellent yields.

Palladium-catalyzed aerobic oxidative coupling of enantioenriched primary allylic amines with sulfonyl hydrazides leading to optically active allylic sulfones

A range of highly enantioenriched primary allylic amines underwent palladium-catalyzed oxidative coupling with sulfonyl hydrazides open to air at room temperature to give structurally diverse allylic sulfones in moderate to excellent yields with excellent retention of ee.

Revealing the metal-like behavior of iodine: an iodide-catalysed radical oxidative alkenylation

In this work, we have described an alternative alkenylation approach to illustrate the metal-like behaviour of iodine in cross-coupling reactions. Alkenylation could proceed through iodide catalysed radical initiation, radical addition and iodine promoted alkenyl functionality recovery. Catalytic HI elimination similar to the β-hydride elimination of transition metals was realized for the radical alkenylation of sulfonyl hydrazides. Operando IR and cyclic voltammetry experiments were carried out to confirm the crucial role of iodine in the radical alkenylation process.

ChemInform Abstract: Regioselective Hydrothiolation of Alkynes by Sulfonyl Hydrazines Using Organic Ionic Base—Broensted Acid.

AbstractNotable advantages of the novel title method are the use of sulfonyl hydrazides as thiol equivalents, excellent regioselectivity, short reaction times, and the use of a recyclable ionic liquid.

Convenient MW-Assisted Synthesis of Unsymmetrical Sulfides Using Sulfonyl Hydrazides as Aryl Thiol Surrogate

An efficient synthesis of unsymmetrical sulfides has been achieved via the cross-coupling reaction of aryl/het-aryl/benzyl halides with stable and easily workable sulfonyl hydrazides as thiol substitutes by means of [DBU][HOAc] and CuI under microwave irradiation.

ChemInform Abstract: Iodine‐Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides.

AbstractAn unprecedented sulfenylation of indoles with sulfonyl hydrazides proceeds through the cleavage of the sulfur—oxygen and the sulfur—nitrogen bond.

Regioselective Hydrothiolation of Alkynes by Sulfonyl Hydrazides Using Organic Ionic Base–Brønsted Acid

A practical and novel approach has been developed for the synthesis of vinyl sulfides by the reaction of sulfonyl hydrazides with aryl/heteroarylacetylenes using a DBU-based ionic liquid. The system offers a new sulfur source for hydrothiolation and is endowed with green credentials.

Iodine‐Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides

Neue Schwefelquelle: Sulfonylhydrazide reagieren in Gegenwart von 10 Mol-% I2 bereitwillig mit Indolen und ergeben eine Bandbreite von Indolthioethern mit hoher Regioselektivität. Diese Reaktion ebnet den Weg zur Verwendung von Sulfonylhydraziden als charakteristische Schwefel-Elektrophile in der chemischen Synthese. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Iodine‐Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides

An unprecedented sulfenylation of indoles with sulfonyl hydrazides proceeds through the cleavage of the sulfur—oxygen and the sulfur—nitrogen bond.

Synthesis of N-substituted derivatives of arylsulfonyl hydrazides and their investigation as additives for lubricating oils

The reaction between arylsulfonyl chlorides and hydrazine has been studied, and it has been found that in the presence of excess hydrazine, the bis-derivatives are produced in small amounts along with monoarylsulfonyl hydrazides. It has been revealed that the reaction of monosulfonyl hydrazides with alkyl bromides in the presence of a base results only in N-alkylation of the sulfamide nitrogen, although the reaction in the presence of HCl proceeds at the amine group with the formation of quaternary ammonium salts. A method for the preparation of sulfonyl hydrazides by oxidation of N-alkyl sulfamides in the presence of iodine has been developed. Some arylsulfonyl hydrazide derivatives have been examined as antioxidant, antirust, and antiwear additives. These sulfonyl hydrazides also exhibit a high bactericidal and fungicidal activity.

Aromatic sulfonyl hydrazides and sulfonyl hydrazones: antimicrobial activity and physical properties

A series of novel aromatic sulfonamide derivatives (1–7) were synthesized and characterized by elemental analyses, FT-IR, 1H NMR, 13C NMR, and LC/MS techniques. The compounds’ quantum mechanical descriptors, surface area, and molecular volume were calculated. All the synthesized compounds were evaluated in vitro as antimicrobial agents against representative strains of gram-positive and gram-negative bacteria and as antifungal agents for yeast by both the disc diffusion and minimal inhibition concentration methods for comparison. All the bacteria and fungi studied were screened against some commercial antibiotics to compare with our chemicals’ zone diameters. Quantitative structure–activity relationship studies with multiple linear regression analysis were applied to find the correlation between the different calculated molecular descriptors of the synthesized compounds and biological activity.

Docking and quantitative structure–activity relationship studies for sulfonyl hydrazides as inhibitors of cytosolic human branched-chain amino acid aminotransferase

We have performed the docking of sulfonyl hydrazides complexed with cytosolic branched-chain amino acid aminotransferase (BCATc) to study the orientations and preferred active conformations of these inhibitors. The study was conducted on a selected set of 20 compounds with variation in structure and activity. In addition, the predicted inhibitor concentration (IC(50)) of the sulfonyl hydrazides as BCAT inhibitors were obtained by a quantitative structure-activity relationship (QSAR) method using three-dimensional (3D) vectors. We found that three-dimensional molecule representation of structures based on electron diffraction (3D-MoRSE) scheme contains the most relevant information related to the studied activity. The statistical parameters [cross-validate correlation coefficient (Q(2) = 0.796) and fitted correlation coefficient (R(2) = 0.899)] validated the quality of the 3D-MoRSE predictive model for 16 compounds. Additionally, this model adequately predicted four compounds that were not included in the training set.

An Efficient Synthesis of Sulfonylhydrazides and Sulfonylsemicarbazides by Utilizing Alumina as a Catalyst

AbstractSulfonyl hydrazides and sulfonyl semicarbazides are readily prepared by the reacting of hydrazine derivatives with sulfonyl chlorides in the presence of basic alumina under solvent‐free conditions. Reaction of a sulfonyl chloride with t‐butylcarbazate, followed by hydrolysis provides the corresponding sulfonyl hydrazides in higher yield and shorter time than previously reported.

Copper patterned polystyrene panels by reducing of surface bound Cu (II)-sulfonyl hydrazide complex

A modified electroless metal deposition method has been developed for copper plating of polystyrene (PS) surfaces. The modified procedure avoids the plasma conditioning and surface activation steps in the classical electroless metal plating process. First step of the present procedure is chlorosulfonation of PS surface by soaking into chlorosulfonic acid, yielding chlorosulfonated surface with density of 0.046–0.110 mmolcm − 2 depending on contact time (10–60 min). In the second step chlorosulfone groups on the surface are converted to sulfonyl hydrazides almost quantitatively by reaction with hydrazine solution (80%). Green Cu (II)-sulfonylhydrazide complex is formed at the surface, in the third step, by interaction with ammoniacle Cu (II) solution at room temperature. The copper in the complex is reduced rapidly in the fourth step, by immersing the specimen into 5% of hydrazine solution. The elemental copper deposited onto the surface serves activating sites to accumulate more (5–7 mg per cm 2) elemental copper from electroless copper solutions in the final step. The present method avoids the surface activation with palladium and allows preparing copper patterns with reasonably high pull-off strengths (3.77 Nmm − 2 ) on PS panels. In the study the copper deposition has been investigated using standard analytical procedures, X-ray photoelectron spectrometry (XPS) and Scanning Electron Microscopy.

Semisynthetic Derivatives of Madurahydroxylactone and Their Antibacterial Activities.

Madurahydroxylactone is a secondary metabolite from Nonomuria rubra (former Actinomadura rubra) with in vitro activity against gram-positive bacteria and belongs to the family of benzo[a]naphthacenequinones. A series of derivatives of madurahydroxylactone were synthesized to investigate the effect on the antibacterial activity. Reaction with alcohols and amines gave cyclic acetals or aminals derived from the lactone form, whereas other amino reagents like hydroxylamines and acyl or sulfonyl hydrazides led to the corresponding imine derivatives of the aldehyde. Hydrazine, alkyl and aryl hydrazines react with madurahydroxylactone under cyclization to give compounds of the new heterocyclic basic structure naphthaceno[1,2-g]phthalazine. Some new compounds strongly inhibit gram-positive bacteria, in part stronger than the parent compound.

Potential Antitumor Agents via Inhibitors of L-Asparagine Synthetase: Substituted Sulfonamides and Sulfonyl Hydrazides Related to Glutamine

A series of 4-(substituted aminosulfonyl)-and 4-(substituted hydrazinosulfonyl)-2-aminobutanoic acids, compounds structurally related to glutamine, was synthesized as potential inhibitors of L-asparagine synthetase and subjected to screening as antitumor agents. Target amino acids were obtained by condensation of a blocked reactive sulfonyl chloride with the appropriate amine or hydrazide, followed by deblocking with hydrogen-palladium or liquid hydrogen fluoride-anisole. Neither the target compounds nor their protected precursors inhibited the enzyme from L5178Y/AR or prolonged the life of mice with P-388 lymphocytic leukemia. However, DL-4,4′-dithiobis[2-(benzyloxycarbon- ylamino)butanoic acid], an intermediate in the synthesis of the target amino acids, exhibited 90% inhibition of L-asparagine synthetase at 10mM.

Synthesis of a few Sulfonyl hydrazides and Acid hydrazides and their Derivatives from Acenaphthene sulfonyl chloride as Antibacterial Agents

Synthesis of a few Sulfonyl hydrazides and Acid hydrazides and their Derivatives from Acenaphthene sulfonyl chloride as Antibacterial Agents