2144-00-5

Usage

Uses

Used in Organic Synthesis:
Naphthalene-1-carbaldehyde (1-naphthylmethylene)hydrazone is used as a starting material for the production of dyes and pharmaceuticals due to its strong reactivity and diverse applications in organic chemistry.
Used in Analytical Chemistry:
naphthalene-1-carbaldehyde (1-naphthylmethylene)hydrazone is used as a chelating agent for the determination of certain metals, making it a valuable tool in analytical chemistry.
Used in the Preparation of Heterocyclic Compounds:
Naphthalene-1-carbaldehyde (1-naphthylmethylene)hydrazone is used as a reagent in the preparation of various heterocyclic compounds, contributing to the development of new chemical entities.
Used as a Fluorescent Chemosensor:
naphthalene-1-carbaldehyde (1-naphthylmethylene)hydrazone has the potential to act as a fluorescent chemosensor for the detection of various analytes, making it a promising candidate for applications in chemical sensing and analysis.

InChI:InChI=1/C22H16N2/c1-3-13-21-17(7-1)9-5-11-19(21)15-23-24-16-20-12-6-10-18-8-2-4-14-22(18)20/h1-16H/b23-15+,24-16+

Upstream product

• 66-77-3 1-naphthaldehyde 
• 86-53-3 1-Cyanonaphthalene 
• 75-69-4 trichlorofluoromethane 
• 19350-73-3 4-methyl-N'-(naphthalen-1-ylmethylene)benzenesulfonohydrazide 
• 91-20-3 naphthalene 
• 52023-52-6 N,N,N',N'-tetraformylhydrazine 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 
• 16430-29-8 naphthalen-1-ylmethylene-hydrazone 
• 354-58-5 1,1,1-Trichloro-2,2,2-trifluoroethane 
• 26153-26-4 1-naphthylglyoxylic acid 
• 33656-65-4 ethyl 2-(1-naphthyl)-2-oxoacetate 

Downstream Products

• 66-77-3 1-naphthaldehyde 
• 4743-58-2 (3-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid 
• 86-55-5 1-naphthalenecarboxylic acid 

Relevant academic research and scientific papers

Synthesis, characterization and biological activity evaluation of novel naphthalenylmethylen hydrazine derivatives as carbonic anhydrase inhibitors

In the current study some derivatives of naphthalenylmethylen hydrazine were synthesized and possible in vitro hCA I and II enzymes inhibition effects were investigated. The designed compounds were synthesized by condensation of phenylhydrazine with 1-naphthaldehyde or 6-methoxy-2-naphthaldehyde and eight compounds (1a-h) were obtained. The novel Schiff bases derivatives (compounds 1a-1h) were effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II) with Ki values in the range of 80.60 ± 17.90 to 492.53 ± 95.23 nM for hCA I, 102.88 ± 18.44 to 461.09 ± 102.50 nM for hCA II. 1f compound shows a remarkable inhibitory effect of hCA I and hCA II isoenzymes among the new synthesized compounds. The new derivatives of naphthalenylmethylen hydrazine can be a potent inhibitor of both cytosolic CA isoenzymes which are commonly used in the pharmaceutical industries and medical areas.

Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines

Herein, an efficient and simple catalytic method for the selective and partial reduction of aldazines using ruthenium catalyst [Ru(p-cymene)Cl2]2 (1) has been accomplished. Under mild conditions, aldazines undergo the addition of pinacolborane in the presence of a ruthenium catalyst, which delivered N-boryl-N-benzyl hydrazone products. Notably, the reaction is highly selective, and results in exclusive mono-hydroboration and desymmetrization of symmetrical aldazines. Mechanistic studies indicate the involvement of in situ formed intermediate [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1a) in this selective hydroboration.

Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions

Abstract: A facile, environmentally and efficient Cs2CO3-mediated decomposition of N-tosylhydrazones reaction has been developed for the synthesis of functionalized azines under mild conditions. This method offers broad substrate scope, occurs as additive-free, without strong base conditions, utilizes readily available reactants, and forms products in good to high yields. Graphical Abstract: [Figure not available: see fulltext.]

Utility of nitriles in synthesis of pyrido[2,3-d]pyrimidines, thiazolo[3,2-a]pyridines, pyrano[2,3-b]benzopyrrole, and pyrido[2,3-d] benzopyrroles

3-Aryl-2-cyanoacrylonitriles (1a,b) reacted with 6-aminothiouracil, 2-ethoxy carbonylmethyl-4-oxo-Δ2-thiazoline, 2-cyanomethyl-4-oxo-Δ2- thiazoline and indan-2-one to give pyrido[2,3-d]pyrimidines, thiazolo[3,2-a]pyridines, pyrano [2,3-b]benzopyrrole and pyrido[2,3-b] benzopyrrole, respectively. The IR, MS and 1H-NMR of the synthesized compounds were discussed. The antimicrobial activity of some of the synthesized compounds was tested. Copyright Taylor & Francis Group, LLC.

Orthoamide, LX [1]. N,N,N',N'-Tetraformylhydrazine- a Formylation Agent for Aromatic Compounds of Wide Scope

The reagent system formed from N,N,N',N'-tetraformylhydrazine (3) and aluminum chloride allows the formylation of aromatic compounds. The scope of the method is comparable with the Olah formylation and the Gross-Rieche procedure, since benzene and fluorobenzene can be formylated. Two formyl groups are transferred from 3 to the aromatic nuclei when a molar ratio 4:1:4 (aluminum chloride/3/aromatic compound) is chosen.

A novel approach to 2-chloro-2-fluorostyrenes

A new general catalytic olefination reaction (COR) of aromatic and heteroaromatic aldehydes and ketones was applied to synthesise 2-chloro-2-fluorostyrenes. The two-stage procedure includes the transformation of carbonyl compounds into hydrazones followed by treatment with CFCl3 mediated by copper catalysis. Trichlorofluoromethane was used as a chlorofluoromethylene transfer reagent. The reaction proceeds stereoselectively and the target alkenes were obtained in high yield. A proposed mechanism for the reaction is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

A novel approach to fluoro-containing alkenes

A new and general one-pot transformation of aromatic aldehydes to fluorinated olefins containing -CH=C(Cl)CF3 or -CH=C(F)CClF2 moieties is described. Freons CCl3CF3 and CCl2FCClF2 were used as trifluoromethyl and difluoromethyl C2-building blocks respectively. A proposed mechanism for the reaction is discussed.

One-pot oxidation of azomethine compounds into arenecarboxylic acids

Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.

Fully conjugated and soluble polyazomethines containing 1.1′ binaphthyl groups

Four monomers containing azomethine linkages and 1-naphthyl groups at the extremities were synthesized by coupling reaction of 1-naphthylaldehyde or 1-naphthylamine with two diamines and two dialdehydes, respectively. The corresponding polymers were obtained by chemical oxidation using anhydrous FeCl3. Both monomers and polymers were investigated by IR, UV and 1H-NMR methods.

Oxidative Transformations of Aldazines and Ketazines with Organic Peroxyacids

Oxidation of aromatic aldazines and ketazines with various peroxycarboxylic acids was investigated.It was found that one part of azine molecule 2 was converted into carbonyl compound 1 or related acid 3 while the second part was transformed into carboxylic ester 4 related to peroxyacid used as an oxidant.It was revealed that aromatic azines could be used as a source of diazaarylmethanes and mechanisms of reactions studied were postulated. aldazines, carboxylic esters, ketazines, oxidation, peroxycarboxylic acids