101336-63-4Relevant articles and documents
Synthesis and insecticidal bioactivities of 2,3-dihydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
Zhang, Letian,Liu, Kun,Shao, Xusheng,Li, Zhong,Xu, Xiaoyong
, p. 340 - 344 (2019)
A novel synthesis of 2,3-dihydroimidazo[1,2-a]pyridin-5(1H)-one 4 and its derivatives were described. Preliminary bioassays showed that some of the target compounds exhibited excellent insecticidal activities against brown planthopper (Nilaparvata lugens), cowpea aphids (Aphis craccivora) (4, 5a, 5c, 5g, 5h, 5j, 5r, 6b, 6e) and carmine spider mite (Tetranychus cinnabarinus (5f, 5s, 6a) at 500 mg/L. Among them, compound 4 was still active against brown planthopper and cowpea aphids at 4 mg/L. The insecticidal activities were influenced by the types and position of the substituents, which provided guidance for the structure modifications.
Oxidation strategy for the synthesis of regioisomeric spiroisobenzofuranopyrroles: Facile entries to spiro[isobenzofuran-1,2′-pyrrole] and Spiro[isobenzofuran-1,3′-pyrrole] derivatives
Fan, Yefeng,Liu, Song,Chen, Nanyang,Shao, Xusheng,Xu, Xiaoyong,Li, Zhong
, p. 393 - 403 (2015)
Two practical and efficient approaches have been developed to synthesize two kinds of racemic spiroisobenzofuranopyrrole analogues as regioisomers. In the presence of sodium periodate, cis-indeno[1,2-b]pyrrol-4(1H)-ones were converted into spiro[isobenzofuran-1,2′-pyrrole] derivatives by a two-step process. In addition, oxidative reactions promoted by lead tetraacetate were demonstrated using cis-indeno[2,1-b]pyrrol-8(1H)-ones as substrates, affording spiro[isobenzofuran-1,3′-pyrrole] derivatives. The remarkable features of two approaches included mild and convenient reaction conditions, a broad substrate scope, and moderate to excellent yields. Possible mechanisms were proposed based on the comparison of the intermediates and products.
[6-chloro-3-pyridylmethyl-3H]neonicotinoids as high-affinity radioligands for the nicotinic acetylcholine receptor: Preparation using NaB3H4 and LiB3H4
Latli, Bachir,Than, Chit,Morimoto, Hiromi,Williams, Philip G.,Casida, John E.
, p. 971 - 978 (1996)
NaB3H4, and LiB3H4 at 78% and 97% isotopic enrichments, respectively, were used in the synthesis of 3H-labeled 1-(6-chloro-3-pyridyl)-methyl-2-nitromethyleneimidazolidine (CH-IMI) and N'-[(6-chloro-3-pyridyl)methyl]-N''-cyano-N'-methylacetamide (acetamiprid) (two very potent insecticides) and of 1-(6-chloro-3-pyridyl)methyl-2-iminoimidazolidine (desnitro-IMI) (a metabolite of the commercial insecticide imidacloprid). 6-Chloronicotinoyl chloride was treated with either NaB3H4 in methanol or LiB3H4 in tetrahydrofuran and the resulting alcohol transformed to 2-chloro-5-chloromethylpyridine, which was then coupled to N-cyano-N'-methylacetamidine to give [3H]acetamiprid (45 Ci/mmol). 2-Chloro-5-chloro [3H]methylpyridine was also reacted with ethylenediamine and the product was either refluxed in absolute ethanol with 1,1-bis(methylthio)-2-nitroethylene to provide [3H]CH-IMI or reacted in toluene with a solution of cyanogen bromide to produce [3H]desnitro-IMI (each 55 Ci/mmol).
One-pot synthesis chloropyridine nitro methylene imidazolidine method
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Paragraph 0021-0031, (2019/10/22)
The invention provides a method for synthesizing chloronitropyridine methyleneimidazolidine through a one-pot process. The synthetic method adopted in the invention is characterized in that the structural formula is as shown in the specification, chloronitropyridine methyleneimidazolidine is synthesized by virtue of the one-pot process, the intermediate of the reaction in each step does not need to be separated and purified, the operations of all synthesis units are finished in the same reaction kettle, the equipment utilization rate is high, the after-treatment process is simple and convenient, the operation conditions are mild, and the three wastes are greatly reduced. The product is recrystallized by virtue of an organic solvent, the content of the product is 98 percent, and the method has good industrial production prospects.
One-pot process for preparing 2 - chloro -5 - ((2 - (nitro-methylene) imidazoline -1 - yl) methyl) pyridine (by machine translation)
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Page/Page column 6-8, (2019/03/06)
The present invention discloses a one-pot process for preparing 2 - chloro - 5 - ((2 - (nitro-methylene) imidazoline - 1 - yl) methyl) pyridine method, in order to 2 - chloro - 5 - chloromethyl pyridine as the starting material, directly with ethylenediamine to generate condensation reaction, the system results in the chlorine [...] ethylenediamine; chloro [...] ethylene diamine and 1, 1, 1 - trichloro - 2 - nitroethane in the presence of acid, cyclization to obtain the target product. The method avoid the use of expensive reagent such as phase transfer catalyst, the use of ethylenediamine is easy to be recycled, this craft is friendly to the environment; the method of the reaction raw material, mild reaction conditions, the reaction step is simple, easy to operate, the total yield is relatively high, in particular, the intermediate does not need of separation and purification, therefore the equipment utilization is high; according to the method the production of target product purity up to 98% or more. In short, the one-pot process for preparing 2 - chloro - 5 - ((2 - (nitro-methylene) imidazoline - 1 - yl) methyl) pyridine method is very suitable for large-scale industrial production. (by machine translation)
2 - Chloro - 5 - ((2 - (nitro-methylene) imidazolidine - 1 - yl) methyl) pyridine synthesis process
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Paragraph 0192; 0193; 0194; 0196; 0197; 0198, (2018/03/26)
The invention provides a synthesis process of 2-chlorin-5-((2-(nitryl methylene) imidazoline-1-yl) methyl) pyridine. Particularly, the method comprises the following steps: preparing 2-nitryl methylene imidazolidine from vinylidene chloride serving as a raw material; and reacting the 2-nitryl methylene imidazolidine with a 2-chlorin-5-chloromethyl pyridine compound so as to form 2-chlorin-5-((2-(nitryl methylene) imidazoline-1-yl) methyl) pyridine. The synthesis process has the advantages that raw materials are easily available, production cost is low, conditions are mild, and the operation is simple and convenient; moreover, synthesis process is environmentally-friendly and suitable for industrial production.
Synthesis and insecticidal evaluation of tetrahydroimidazo[1,2-a]pyridin-5(1H)-one derivatives
Liu, Xuan-Qi,Liu, Ya-Qin,Shao, Xu-Sheng,Xu, Zhi-Ping,Xu, Xiao-Yong,Li, Zhong
, p. 7 - 10 (2016/01/25)
A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (=CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L-1. Among them, compound 11h was active against brown planthopper at 100 mg L-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.
Synthetic method of 2-chlorine-5-((2-(nitromethylene)imidazoline-1-yl)methyl)pyridine
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Paragraph 0040; 0041, (2016/10/09)
The invention provides a synthetic method of 2-chlorine-5-((2-(nitromethylene)imidazoline-1-yl)methyl)pyridine. The method comprises the steps of taking 2-chlorine-5-nitrapyrin as a starting material, enabling the starting material to be subjected to a substitution reaction with ethylenediamine in the presence of a phase transfer catalyst and alkali to generate chloropyridine ethylenediamine, adding 1,1-dimethoxy-2-nitroethylene into the same reaction vessel, performing a reflux reaction, performing after-treatment to prepare a target product, i.e., the 2-chlorine-5-((2-(nitromethylene)imidazoline-1-yl)methyl)pyridine is synthesized by a one-pot method. By adopting the synthetic method, the target product of high content can be obtained, an intermediate of the first-step reaction does not need separation and purification, the two-step synthesis unit operation is completed in the same reaction vessel, the equipment utilization rate is high, the after-treatment is simple in process, the operation conditions are mild, thus a prospect of industrial production is achieved.
Synthesis and insecticidal activities of tetrahydroimidazo[1,2-a] pyridinones: Further exploration on cis-neonicotinoids
Ren, Liping,Lou, Yanpeng,Chen, Nanyang,Xia, Shanshan,Shao, Xusheng,Xu, Xiaoyong,Li, Zhong
, p. 858 - 867 (2014/03/21)
cis-Neonicotinoid, in which the nitro and cyano pharmacophore point to the same position relative to the heteroaromatic moiety, is a further extension of the neonicotinoid library. While seeking new cis-neonicotinoid candidates, a series of tetrahydroimidazo[1,2-a]pyridinone derivatives were synthesized by reactions of nitromethylene analogs with itaconic anhydride. All the compounds were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectroscopy. The target compounds had excellent insecticidal activities against cowpea aphids (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Against armyworm, most of the compounds showed moderate activities. Interestingly, compound 12p was active against Tetranychus cinnabarinus. The synthesized compounds displayed good insecticidal activities against different insect species, which might provide useful guidance for further design of cis-neonicotinoid candidates. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Designing tetrahydroimidazo[1,2- a ]pyridine derivatives via catalyst-free Aza-Diels-Alder Reaction (ADAR) and their insecticidal evaluation
Zhang, Wenwen,Chen, Yinbo,Chen, Weidong,Liu, Zewen,Li, Zhong
scheme or table, p. 6296 - 6299 (2011/08/05)
A series of tetrahydroimidazo[1,2-a]pyridine derivatives were synthesized by the reaction of 2-vinyl-4,5-dihydroimidazole derivatives with substituted benzylidenemalononitrile via a catalyst-free aza-Diels-Alder reaction. Insecticidal activities of target
