- One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones by a Smiles Rearrangement
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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.
- Jiang, Xiaolei,Hu, Fangdong
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supporting information
p. 1207 - 1210
(2018/03/23)
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- A thiadiazole compounds and its synthetic method
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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.
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Paragraph 0032; 0033; 0034; 0035; 0036; 0037; 0038; 0059
(2019/02/02)
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- A oxadiazole compound and its preparation method
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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.
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Paragraph 0034; 0038; 0039; 0040
(2017/04/14)
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- Functionalization of 4,5-Dichloropyridazin-3(2H)-one
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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.
- Sung, Gi Hyeon,Kim, Bo Ram,Ryu, Ki Eun,Yoon, Yong-Jin
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p. 140 - 144
(2014/04/03)
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- Access to 4-alkylaminopyridazine derivatives via nitrogen-assisted regioselective pd-catalyzed reactions
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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.
- Blaise, Emilie,Kümmerle, Arthur E.,Hammoud, Hassan,De Arajo-Jnior, Jo Xavier,Bihel, Frdric,Bourguignon, Jean-Jacques,Schmitt, Martine
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p. 10311 - 10322
(2015/02/19)
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- PYRIDAZINONE GLUCOKINASE ACTIVATORS
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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.
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Page/Page column 47
(2009/10/30)
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- Novel formation of 1,3-oxazepine heterocycles via palladium-catalyzed intramolecular coupling reaction
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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.
- Ma, Chen,Liu, Shao-Jie,Xin, Liang,Falck,Shin, Dong-Soo
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p. 9002 - 9009
(2007/10/03)
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- ZnCl2-mediated synthesis of carboxylic anhydrides using 2-acyl-4,5-dichloropyridazin-3(2H)-ones
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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
- Park, Yong-Dae,Kim, Jeum-Jong,Kim, Ho-Kyun,Cho, Su-Dong,Kang, Young-Jin,Park, Ki Hun,Lee, Sang-Gyeong,Yoon, Yong-Jin
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p. 371 - 378
(2007/10/03)
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- 2-Cyanopyridazin-3(2H)-ones: Effective and chemoselective electrophilic cyanating agents
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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.
- Kim, Jeum-Jong,Kweon, Deok-Heon,Cho, Su-Dong,Kim, Ho-Kyun,Jung, Eun-Young,Lee, Sang-Gyeong,Falck,Yoon, Yong-Jin
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p. 5889 - 5894
(2007/10/03)
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- Pyridazines. Part 35: Traceless solid phase synthesis of 4,5- and 5,6-diaryl-3(2H)-pyridazinones
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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.
- Sotelo, Eddy,Ravi?a, Enrique
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p. 1113 - 1116
(2007/10/03)
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- Retro-ene reaction. II. Reaction of 4,5-dichloro-1-hydroxymethylpyridazin-6-one with alkyl halides and carboxylic acid chlorides
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1-Alkyl-4,5-dichloropyridazin-6-ones and (4,5-dichloro-6-oxopyridazin-1-yl)methylcarboxylates were synthesized from 4,5-dichloro-1-hydroxymethylpyridazin-6-one and the corresponding alkyl halides or carboxylic acid chlorides. Also the reaction mechanisms via a fragmentation of retro-ene type are discussed.
- Kim, Sung-Kyu,Cho, Su-Dong,Kweon, Deok-Heon,Lee, Sang-Gyeong,Chung, Joo-Wha,Shin, Sung Chul,Yoon, Yong-Jin
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p. 245 - 248
(2007/10/03)
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- 3(2H)-pyridazinone compounds derivatives and compositions for controlling and/or preventing insect pests intermediates for such compounds, and a process for their manufacture
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A novel 3(2H)-pyridazinone derivative of the formula [I]: STR1 wherein, R represents an alkenyl group having 2 to 16 carbon atoms, an alkynyl group having 2 to 16 carbon atoms, an alkyl group having 3 to 8 carbon atoms substituted by an alkoxy group having 1 to 6 carbon atoms or G-Ra-; A represents hydrogen atom, halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms or an alkylsulfonyl group having 1 to 4 carbon atoms; R1 represents hydrogen atom, halogen atom, an alkoxy group having 1 to 4 carbon atoms or hydroxyl group; X represents oxygen or sulfur atom; J represents STR2 as well as insecticidal, acaricidal and nematicidal compositions and compositions for expelling ticks parasitic on animals, said compositions containing as an active ingredient at least one of the above derivatives.
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- Pyridazinylurea plant regulators
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Pyridazinylurea plant regulators of the formula STR1 and acid addition salts thereof; wherein R is alkyl or cycloalkyl, R1 is hydrogen or alkyl, each X independently is halogen, alkoxy, alkylthi or alkylsulfonyl, and p is 0, 1 or 2.
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- Synthesis of analogues of the 2,3,6-triazaphenothiazine ring system
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Treatment of 2,3-dichloroquinoxalines with 2-amino-6-picoline-3-thiol gave a mixture of 2,3-bis(2-amino-6-picolinyl-3-thio)quinoxalines (16, R = H, Cl) and 2,3-bis (N,N-dimethylamino)quinoxalines (15, R = H, Cl) separated by fractional crystallization. A similar reaction of 3-amino-6-methoxypyridine-2(1H)-thione (9) with 4,5-dichloropyridazin-3(2H)-one (21) gave 4-chloro-5-(3-amino-6-methoxypyridyl-2-thio)pyridazin-3(2H)-one (22). Concentrated hydrochloric acid-catalysed cyclization of 22 gave the nonrearranged 7-methoxy-2,3,6-triazaphenothiazin-1(2H)-one. The action of compound 22 in refluxing glacial acetic acid gave, on the other hand, 7-methoxy-2,3,6-triazaphenothiazin-4(3H)-one via a Smiles rearrangement. These cyclized compounds are the first known derivatives of the new 2,3,6-triazaphenothiazine ring system.
- Okafor,Castle
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p. 199 - 203
(2007/10/02)
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- S-Demethylation of Nitrogen Heterocycles
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When 3-chloro-4,5-diaminopyridazine (2) was treated with sodium methylmercaptide in refluxing N,N-dimethylformamide, two heterocycles were formed and isolated, neither of which was the expected 3-methylthio-4,5-diaminopyridazine (3).A thorough spectral analysis of these heterocycles showed them to be 4-methylthioimidazopyridazine (5) and imidazopyridazine-4-thione (6).N,N-Dimethylformamide was found to provide the one carbon unit required for the formation of 5.The origin of 6 was shown to be a result of S-demethylation of 5.S-Demethylation of 3 could also be effected with sodium methylmercaptide in methyl sulfoxide without the occurrence of annulation.In methyl sulfoxide the process of demethylation was accelerated and occurred at lower temperature.
- Chen, Shih-Fong,Panzica, Raymond P.
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p. 303 - 307
(2007/10/02)
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