932-22-9

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dichloro-3(2H)-pyridazinone is used as a tuberculostatic agent for its ability to inhibit the growth of Mycobacterium tuberculosis, making it a potential candidate for the development of new antituberculosis drugs.
Used in Research and Development:
4,5-Dichloro-3(2H)-pyridazinone is used as a research compound for studying its tuberculostatic properties and exploring its potential as a new therapeutic agent for tuberculosis treatment.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 385, 1991 DOI: 10.1002/jhet.5570280234

InChI:InChI=1/C4H2Cl2N2O/c5-2-1-7-4(9)8-3(2)6/h1H,(H,7,8,9)

Upstream product

• 14161-11-6 3,4,5-trichloropyridazine 
• 87-56-9 mucochloric acid 
• 134541-32-5 4,5-Dichloro-2-(1,1-dibromo-2-oxo-propyl)-2H-pyridazin-3-one 
• 51355-97-6 4,5-dichloro-2-(hydroxymethyl)pyridazin-3(2H)-one 
• 155164-66-2 2-benzoyl-4,5-dichloropyridazin-3(2H)-one 
• 155164-67-3 4,5-Dichloro-2-(4-methyl-benzoyl)-2H-pyridazin-3-one 
• 155164-68-4 4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one 
• 450408-65-8 4,5-dichloro-2-hexanoyl-2H-pyridazin-3-one 
• 450408-66-9 4,5-dichloro-2-(4-chloro-benzoyl)-2H-pyridazin-3-one 
• 123-30-8 4-amino-phenol 
• 859214-48-5 2-cyano-4,5-dichloropyridazin-3(2H)-one 
• 108-91-8 cyclohexylamine 
• 109-73-9 N-butylamine 
• 62-53-3 aniline 

Downstream Products

• 504-30-3 2H-Pyridazin-3-one 
• 55271-58-4 4-amino-5-chloro-2H-pyridazin-3-one 
• 6339-19-1 5-amino-4-chloropyridazin-3(2H)-one 
• 14161-11-6 3,4,5-trichloropyridazine 
• 100563-02-8 4,5-dichloro-2-(2-morpholinoethyl)pyridazin-3(2H)-one 
• 62688-74-8 10-acetyl-8-nitro-3H,10H-benzo[b]pyridazino[4,5-e][1,4]thiazin-4-one 
• 55271-55-1 3H,10H-dipyridazino[4,5-b;4',5'-e][1,4]thiazin-4-one 
• 13617-04-4 2H,7H-[1,4]dithiino[2,3-d;5,6-d']dipyridazine-1,6-dione 
• 153276-34-7 4-chloro-5-(piperazin-1-yl)-2,3-dihydropyridazin-3-one 
• 82412-97-3 4-chloro-5-<(2-hydroxyethyl)methylamino>-3(2H)-pyridazinone 
• 51659-49-5 1-Butyl-4,5-dichlor-pyridazon 
• 85302-02-9 1-oxo-1,2-dihydro-2,3-diazaphenoxathiin 
• 85302-01-8 4-oxo-3,4-dihydro-2,3-diazaphenoxathiin 
• 92574-75-9 2-((benzyloxy)methyl)-4,5-dichloropyridazin-3(2H)-one 

Relevant academic research and scientific papers

One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones by a Smiles Rearrangement

A simple and convenient synthesis of indole-fused pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones is described. A range of 2-(1 H -indol-2-yl)phenols and 4,5-dichloropyridazin-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.

A thiadiazole compounds and its synthetic method

The invention relates to a thiadiazole compound and a synthesis method thereof. Alkoxy sodium xanthate is synthesized from an alcohol compound, sodium hydroxide and carbon disulfide, alkoxy thiocarbonyl hydrazine is synthesized from alkoxy sodium xanthate and hydrazine hydrate, and N'-alkoxyl thiocarbonyl-N-2-chloroacetylhydrazide is synthesized from alkoxy thiocarbonyl hydrazine and 2-chloroacetyl chloride; 2-alkoxyl-5-chloromethyl-1,3,4-thiadiazole is synthesized through cyclization of the generated hydrazide compound under an action of concentrated sulfuric acid and then undergoes a reaction with 4,5-dichloro-3(2H)pyridazinone, and the generated intermediate undergoes a substitution reaction with aliphatic amine or cyclic aliphatic amine or propyl sulfhydrate under catalysis of an alkaline reagent to synthesize a bishydrazide derivative. Compared with the prior art, the thiadiazole compound has the advantages of simple technological process and wide application range, is suitable for use in prevention and treatment of sanitary pests such as flies, mosquitoes, fleas and the like and prevention and treatment of other agricultural pests such as rice water weevils, beet armyworm, plutella xylostella, armyworm and the like, and is an insecticide having an application prospect.

A oxadiazole compound and its preparation method

The present invention relates to an oxadiazole compound and a preparation method thereof, wherein the molecular formula of the compound is as the follow, R1 is halogen, hydrogen, C1-C4 alkyl or alkoxy, R2 is halogen, hydrogen or alkyl, and R3 is methylamine, dimethylamine, isopropylamine, propylamine, butylamine, morpholine, piperidine or imidazole. Compared with the oxadiazole compound and the preparation method in the prior art, the oxadiazole compound and the preparation method of the present invention have the following characteristics that: the process is simple, the application range is wide, and the oxadiazole compound is suitable for prevention and control of health pests such as flies, mosquitoes, fleas and the like and agricultural pests such as lissorhoptrus oryzophilus, spodoptera exigua hiibner, mythimna separata (walker) and the like, can be provided for inhibiting growth of insects, especially mosquito larvae, and is an insecticide with an application prospect.

Functionalization of 4,5-Dichloropyridazin-3(2H)-one

The functionalization of 4,5-dichloropyridazin-3(2H)-one and 4,5-dichloro-2-methyl-6-nitropyridazin-3(2H)-one was reported. A mixture of 4,5-dichloropyridazin-3(2H)-one, potassium nitrate and conc-sulfuric acid was stirred for 5 hours at 110-120°C. After cooling to room temperature, the solution was slowly poured into ice-water. The resulting yellow crystals was filtered, washed with water and dried in air to give the product. A mixture of 4,5-dichloro-6- nitropyridazin-3(2H)-one and POCl3 was refluxed for 24 hours. After cooling to room temperature, the solution was evaporated under reduced pressure. The resulting residue was slowly poured into ice-water (300 mL). Chlorination of compound 4,5-dichloro-6- nitropyridazin-3(2H)-one with phosphorus oxychloride also gave 3,4,5-trichloro-6-nitropyridazine in 72% yield. Three proton signals were also detected at d 9.0 (1H), 8.64 (1H) and 6.20 (2H) ppm in the spectrum of 1H NMR.

Access to 4-alkylaminopyridazine derivatives via nitrogen-assisted regioselective pd-catalyzed reactions

3-Substituted, 6-substituted, and unsymmetrical 3,6-disubstituted 4-alkylaminopyridazines were prepared from a sequence of three chemo- and regioselective reactions combining amination and palladium-catalyzed cross-coupling reactions, such as reductive dehalogenation and Suzuki-Miyaura reactions. Extension of the methodology to Sonogashira reaction yielded a novel class of 3-substituted pyrrolopyridazines.

PYRIDAZINONE GLUCOKINASE ACTIVATORS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.

Novel formation of 1,3-oxazepine heterocycles via palladium-catalyzed intramolecular coupling reaction

The oxazepine ring systems containing pyridazinone moiety were constructed via palladium-catalyzed intramolecular coupling reaction. The best conditions for this reaction were Pd(OAc)2 as a palladium source, 1,1′-bis(diphenylphosphino)-ferrocene (DPPF) as the ligand, and K2CO3 as base at 80 °C in toluene. The products have potential applications as biological and medicinal relevant compounds.

2-Cyanopyridazin-3(2H)-ones: Effective and chemoselective electrophilic cyanating agents

2-Cyanopyridazin-3(2H)-ones are novel, effective, selective and electrophilic cyanating agents. A variety of amino, thiol and carbon nucleophiles are chemoselectively N-, S- or C-cyanated in excellent yield using 2-cyanopyridanzin-3(2H)-ones in water or tetrahydrofuran.

ZnCl2-mediated synthesis of carboxylic anhydrides using 2-acyl-4,5-dichloropyridazin-3(2H)-ones

ZnCl2 is an efficient catalyst for synthesis of carboxylic acid anhydride from 2-acyl-4,5-dichloropyridazin-3(2H)-ones. Treatment of 2-acyl-4,5-dichloropyridazin-3(2H)-ones with ZnCl2 (0.5 equivalents) and air in refluxing dry THF or

Pyridazines. Part 35: Traceless solid phase synthesis of 4,5- and 5,6-diaryl-3(2H)-pyridazinones

A new method for the traceless solid phase synthesis of 3(2H)-pyridazinones has been developed employing dihydropyran-functionalized resin. The procedure has permitted the preparation of several diarylpyridazinones through a Suzuki cross-coupling reaction and cleavage conditions that promoted a retro-ene fragmentation.