1011-84-3Relevant articles and documents
Efficient synthesis of 1,2,4-oxadiazine-5-ones via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides
Wang, Gangqiang,Chen, Rongxing,Zhao, Sen,Yang, Liangfeng,Guo, Haibing,Sun, Shaofa,Wang, Jian,Domena, Justin,Xing, Yalan
, p. 2018 - 2020 (2018)
1,2,4-Oxadiazin-5-ones were prepared via [3+3] cycloaddition of in situ generated aza-oxyallylic cations with nitrile oxides in good yields and excellent functional group compatibility. This efficient transformation is metal-free and is promoted by an inorganic base Cs2CO3. In addition, this reaction features simple-operation, mild conditions, and high regioselectivity.
Highly regioselective 1,3-dipolar cycloaddition of 3′-O-propargyl guanosine with nitrile oxide: An efficient method for the synthesis of guanosine containing isoxazole moiety
Kore, Anilkumar R.,Senthilvelan, Annamalai,Shanmugasundaram, Muthian
, (2020)
The 1,3-dipolar cycloaddition reaction of 3′-O-propargyl guanosine with various in-situ generated nitrile oxides in the presence of DMF as a solvent is described. It is noteworthy that the reaction is highly regioselective that affords biologically import
Efficient synthesis of bis-isoxazole ethers via 1,3-dipolar cycloaddition catalysed by Zn/Zn2+ and their antifungal activities
Zhang, Da-Wei,Lin, Feng,Li, Bo-Chao,Liu, Hong-Wei,Zhao, Tian-Qi,Zhang, Yu-Min,Gu, Qiang
, p. 1500 - 1511 (2015)
An efficient method was developed for synthesising isoxazoles. A series of novel bis-isoxazole ether compounds VI, VII and VIII were synthesised starting from different substituted aldehydes (I) via a 1,3-dispolar cycloaddition using Zn/Zn2+ as a catalyst; these were characterised by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. In addition, the antimicrobial properties of the synthesised products were investigated. The synthesised compounds exhibited significant antifungal activities in comparison with the standard drugs, fluconazole and itraconazole. It was found that Candida albicans was sensitive to 2-substituted phenyl bis-isoxazole ethers bearing pyridyl.
Synthesis and chemical modification of 3,3-dimethyl-1H,3H-furo[4,3- b][1,5]benzothiazepin-1-one
Matsuo,Sunago,Okutani,Takagi,Nakamoto,Kobayashi
, p. 1643 - 1646 (1995)
Heating of 3-(2-aminophenylthio)-2-methoxycarbonyl-4-methyl-2-penten-4- olide with triethylamine hydrochloride gave 3,3-dimethyl-1H,3H-furo[4,3- b][1,5]benzothiazepin-1-one. Some chemical modifications of the product including [2 + 2]cycloaddition and 1,3-dipolar cycloaddition to the imino group in the product were performed.
Synthesis and evaluation of novel isoxazolyl chalcones as potential anticancer agents
Wan, Maosheng,Xu, Linyan,Hua, Li,Li, Ailing,Li, Shuqing,Lu, Wenjing,Pang, Yue,Cao, Chengbo,Liu, Xiangguo,Jiao, Peifu
, p. 38 - 43 (2014)
A series of novel isoxazolyl chalcones were synthesized and evaluated for their activities in vitro against four types of human non-small cell lung cancer cells, including H1792, H157, A549 and Calu-1 cells. The preliminary biological screening showed tha
Cu(I) catalyzed microwave assisted telescopic synthesis of 3,5-disubstituted isoxazoles in green media
Meena,Maiti, Barnali,Chanda, Kaushik
, p. 5514 - 5517 (2016)
A facile and efficient microwave assisted telescopic synthesis of diverse isoxazoles was reported in green reaction medium. Initially, N-hydroxyl imidoyl chlorides were reacted with substituted alkynes in aqueous medium using 2 mol% of [Cu(phen)(PPh3
Safe and scaleable oxidation of benzaldoximes to benzohydroximinoyl chlorides
Hansen, Eric C.,Levent, Mahmut,Connolly, Terrence J.
, p. 574 - 578 (2010)
Benzohydroximinoyl chlorides are useful precursors to nitrile oxides used in the preparation of various heterocycles via 1,3-dipolar cycloadditions. These intermediates are typically accessed by oxidation of aldoximes using N-chlorosuccinimide. This simpl
Reaction of nitrile oxides with vinylphosphonate: A facile, regioselective approach to 5-phosphonyl-4, 5-dihydroisoxazoles
Ye, Yong,Zheng, Yu,Xu, Guo-Yan,Liu, Lun-Zu
, p. 254 - 257 (2003)
The synthesis of 5-phosphonyl-4,5-dihydroisoxazoles from nitrile oxides and diethylvinylphosphonate was discussed. The structure of these compounds were determined by 1H NMR spectroscopy. It was found that the phosphonyl group of dipolarophiles
Reactions of Nitrile Oxides and Nitrilimines with Imidate Esters, the Nitrogen Atom of which forms Part of a Heterocyclic Ring
Miller, David J.,Scrowston, Richard M.,Kennewell, Peter D.,Westwood, Robert
, p. 5159 - 5168 (1994)
The cycloaddition reactions of three cyclic imidate esters, 2-ethoxypyrrolin-5-one (6), 2-ethoxyisoindol-3-one (7) and 2-ethoxy-1H-indol-3-one (8) with various 1,3-dipoles were investigated.Dipolarophile 6 added only to nitrile oxides; 8 added to nitrile
Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction
Pan, Hongmei,Lu, Tong,Wu, Xuedan,Gu, Chengwen,Tao, Naili,Zhang, Biao,Wang, Ao,Chen, Guangmei,Zhang, Kehua,Cheng, Jie,Jin, Jie
, p. 2360 - 2364 (2019/11/11)
A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.
Electrochemical synthesis of 1,2,4-oxadiazoles from amidoximes through dehydrogenative cyclization
Hu, Aixi,Jiang, chan,Li, mingfang,Xu, Leitao,Ye, Jiao,Yi, Yangjie
, p. 10611 - 10616 (2021/12/27)
A convenient and efficient method for the generation of the iminoxy radical through anodic oxidation was developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles fromN-benzyl amidoximes. The transformation proceeds through 1.5-Hydrogen Atom Transfer (1,5-HAT) and intramolecular cyclization. The process features simple operation, mild conditions, broad substrate scope and high functional group compatibility, and provides a facile and practical way for the preparation of 1,2,4-oxadiazoles.