- Efficient and convenient method for the synthesis of isoxazoles in ionic liquid
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An efficient one-pot synthesis of 3,5-disubstitueted isoxazoles from β-diketones in room temperature ionic liquids (ILs) is described. Compared with the classical reaction conditions, this new synthetic method is environmentally friendly and has the advan
- Valizadeh, Hassan,Amiri, Mohammad,Gholipur, Hamid
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- Convenient synthesis of 3,5-disubstituted isoxazoles
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α,β-Unsaturated oximes obtained from the corresponding α,β-unsaturated ketones on treatment with 2 equivalents of manganese dioxide in refluxing chloroform gives 3,5-disubstituted isoxazoles in good yields. Copyright Taylor & Francis Group, LLC.
- Kurangi, Reshma F.,Kawthankar, Rima,Sawal, Sulfala,Desai, Vidya G.,Tilve, Santosh G.
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- SYNTHESIS AND REACTIONS OF 5-(TRIBUTYLSTANNYL)ISOXAZOLES
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3-Substituted 5-(tributylstannyl)isoxazoles were synthesized in good yields by the 1,3-dipolar cycloaddition reaction of ethynyltributylstannane with nitrile oxides generated in situ. 3-Methyl-5-(tributylstannyl)isoxazole was easily converted to the corre
- Kondo, Yoshinori,Uchiyama, Daishi,Sakamoto, Takao,Yamanaka, Hiroshi
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- An improved method for preparation of nitrile oxides from nitroalkanes for in situ dipolar cycloadditions
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A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethylaminopyridine (3) as catalyst in the presence of dipolarophiles
- Basel, Yochai,Hassner, Alfred
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- Reactivity of p-phenyl substituted β-enamino compounds using k- 10/ultrasound. II [1]. Synthesis of isoxazoles and 5-isoxazolones
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The condensation of 4-phenyl substituted β-enamino ketones 1a-d and β- enamino esters 5a-d with hydroxylamine hydrochloride using K-10 as the solid support under sonication was studied to evaluate the formation of isoxazole and 5-isoxazolone rings from β-enamino compounds with a substituted aromatic ring. Isoxazoles 2a-c, 3c-d and 5-isoxazolones 6a-c and 7a-d were obtained. The use of K-10/ultrasound in this reaction furnished novel results in some cases.
- Valduga, Claudete J.,Santis, Denise B.,Braibante, Hugo S.,Braibante, Mara E. F.
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- A photochemical one-pot three-component synthesis of tetrasubstituted imidazoles
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Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, α-aminonitriles, and isoxazoles. Condensation of the first two components produces α-(alkylideneamino)nitriles which react under basic conditions with the acylazirines formed in situ by photochemical ring transformation of the isoxazole component. This process includes an unusual cleavage of the C2-C3 bond of the acylazirine. The reaction mechanism was studied by DFT calculations. (Chemical Equation Presented)
- Pusch, Stefan,Opatz, Till
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- Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles
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Isoxazoles, mainly 3,5-disubstituted, are prepared by catalytic condensation of primary nitro compounds with terminal acetylenes by using a copper/base catalytic system. The additional catalytic effect of the copper(II) salts is evidenced by comparing the kinetic profiles. Selectivity dependence on reaction conditions is considered for phenylacetylene in the following competitive processes: oxidative coupling of terminal alkynes to conjugated diynes catalyzed by CuIIand base in the presence of air; production of furazans beside condensation with benzoylnitromethane to 3-benzoylisoxazoles, as a result of the reaction of the dipolarophile with 3,4-dibenzoylfuroxan; addition of electron-poor alkynes (e.g., methyl propiolate) with themselves and with the nitro compound. Thus, oxidative coupling is negligible in reactions with “active” nitro compounds, whereas with nitroalkanes both products are observed: only trace amounts of isoxazoles are detected without copper. Similarly, in the presence of copper, 3-benzoyl-5-phenylisoxazole is predominant over the furazan. Furthermore, condensations of electron-poor alkynes give complex reaction mixtures in the presence of base alone, but cycloadducts are conveniently prepared with copper. The results indicate the practical and general utility of this catalytic method for synthetic practice.
- Baglieri, Ausilia,Meschisi, Luca,De Sarlo, Francesco,Machetti, Fabrizio
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- NH2OH-HCl-Mediated Umpolung α-Methylsulfonylation of α-Sulfonyl Ketones with Methylsulfoxides: Synthesis of α,β-Bis-sulfonyl Arylketones
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In this paper, a novel and efficient route for the synthesis of α,β-bis-sulfonyl arylketones via an NH2OH-HCl-mediated intermolecular umpolung α-methylsulfonylation of α-sulfonyl ketones with methylsulfoxides is described. A plausible mechanism is proposed and discussed. Various reaction conditions for this efficient, one-pot, environmentally friendly transformation were investigated.
- Chang, Meng-Yang,Chen, Han-Yu,Tsai, Yu-Lin
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- NHC-palladium-catalyzed ionic liquid-accelerated regioselective oxyarylation of alkynes with diaryl ethers?
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The first NHC-palladium-catalyzed regioselective oxyarylation of oxime ether in a task-specific ionic liquid via C(sp3)-O and C(sp2)-O bond cleavage of two different types of ethers for the assembly of structurally diverse 4-arylisoxazoles is described. Both the basic ionic liquid [C3NH2mim]Br and NHC-Pd catalyst IPr-Pd-Im-Cl2 played an important role in this transformation. Notably, this new approach provides a practical and straightforward route to access a broad range of privileged 4-arylisoxazole structures with good yields and excellent regioselectivities. Significantly, this catalytic system can be recycled up to eight times without significant loss of catalytic activity.
- Cen, Liying,He, Dan,Jiang, Huanfeng,Li, Jianxiao,Lin, Zidong,Wu, Wanqing
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supporting information
p. 1983 - 1988
(2022/04/03)
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- AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.
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Page/Page column 58-59
(2020/06/10)
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- A Reusable CNT-Supported Single-Atom Iron Catalyst for the Highly Efficient Synthesis of C?N Bonds
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C?N bond formation is regarded as a very useful and fundamental reaction for the synthesis of nitrogen-containing molecules in both organic and pharmaceutical chemistry. Noble-metal and homogeneous catalysts have frequently been used for C?N bond formatio
- Baell, Jonathan B.,Ding, Qifeng,Huang, Fei,Huang, He,Xu, Mingjie,Yu, Yang,Zhang, Lihui,Zheng, Jian-Guo
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- Preparation method of isoxazole derivative
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The invention relates to a preparation method of an isoxazole derivative, which comprises the following steps of mixing an propargyl alcohol derivative, a halogen source, an acid and a solvent, and heating to react; adding the hydroxylamine into the react
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Paragraph 0125-0130
(2019/12/02)
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- Monohydrochloride Assisted Synthesis of Functionalized Isoxazoles and Pyrazoles from Allenic Ketones: First Synthesis of (Z)-2-Methyl-7H-benzo[b]pyrazolo[5,1-d][1,5]oxazocines
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A facile hydrochloride promoted regioselective synthesis of isoxazoles and pyrazoles from 1,2-allenic ketones is reported. The reaction has been scaled up to gram scale. A direct 8-endo dig ring annulations towards the first synthesis of (Z)-2-methyl-7H-b
- Sarkar, Debayan,Sahoo, Sushree Ranjan
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p. 2035 - 2049
(2019/03/07)
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- TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles
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A TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles was developed, providing 3,5-diarylisoxazoles in good yields. Functional groups such as methoxy, ethyoxyl, chloro, bromo, fluoro and nitro were well tolerated in this reaction
- Abdukader, Ablimit,Sun, Yadong,Zhang, Zengpeng,Liu, Chenjiang
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- Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles
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We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.
- Adamson, Nathan J.,Wilbur, Katherine C. E.,Malcolmson, Steven J.
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supporting information
p. 2761 - 2764
(2018/03/06)
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- Copper-catalyzed aerobic oxidative C-O bond formation for the synthesis of 3,5-disubstituted isoxazoles from enone oximes
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A direct access to 3,5-disubstituted isoxazoles has been accomplished through an intramolecular oxidative coupling reaction of enone oximes using a catalytic quantity of Cu(OAc)2. This method features an inexpensive metal catalyst, molecular ox
- Sun, Yadong,Abdukader, Ablimit,Zhang, Haiyan,Yang, Wanle,Liu, Chenjiang
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p. 55786 - 55789
(2017/12/26)
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- Cycloisomerization of acetylenic oximes and hydrazones under gold catalysis: Synthesis and cytotoxic evaluation of isoxazoles and pyrazoles
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The synthesis of substituted isoxazoles and pyrazoles through a general cycloisomerization methodology has been reported. The capability of gold(III) chloride to promote cycloisomerization of both α, β-acetylenic oximes and α, β-acetylenic hydrazones is t
- Jeyaveeran,Praveen, Chandrasekar,Arun,M Prince,Perumal
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- Direct synthesis of 4-fluoroisoxazoles through gold-catalyzed cascade cyclization-fluorination of 2-alkynone O-methyl oximes
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A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol
- Jeong, Yunkyung,Kim, Bom-I,Lee, Jae Kyun,Ryu, Jae-Sang
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p. 6444 - 6455
(2014/08/05)
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- Synthesis of 3,4,5-trisubstituted isoxazoles through gold-catalyzed cascade cyclization-oxidative alkynylation and cyclization-fluorination of 2-alkynone O-methyloximes
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Gold-catalyzed tandem cyclization-oxidative alkynylation and cyclization-fluorination reactions of 2-alkynone O-methyloximes are described. The reactions proceed smoothly at room temperature in the presence of 10 mol % of (PPh3)AuNTf2, 2.5 equivalents of selectfluor, and 2 equivalents of K3PO4. 2-Alkynone O-methyloximes undergo intramolecular oxyauration/cyclization and ensuing oxidative cross-coupling and fluorination process to afford the corresponding 3,4,5-trisubstituted isoxazoles in a cascade manner.
- Song, Doo-Hee,Ryu, Jae-Sang
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p. 2635 - 2644
(2015/04/22)
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- An efficient synthesis of isoxazoles and pyrazoles under ultrasound irradiation
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A series of 5-arylisoxazole and 5-aryl-1H-pyrazole derivatives was synthesized by the reaction of 3-(dimethylamino)-1-arylprop-2-en-1-one with hydroxylamine hydrochloride or hydrazine hydrate under ultrasound irradiation without using any catalyst. This m
- Huang, Zhi-Bin,Li, Li-Li,Zhao, Yan-Wei,Wang, Hui-Yuan,Shi, Da-Qing
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p. E309-E313
(2014/11/07)
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- Clean and efficient synthesis of isoxazole derivatives in aqueous media
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A series of 5-arylisoxazole derivatives were synthesized via the reaction of 3-(dimethyl-amino)-1-arylprop-2-en-1-ones with hydroxylamine hydrochloride in aqueous media without using any catalyst. This method has the advantages of easier work-up, mild rea
- Dou, Guolan,Xu, Pan,Li, Qiang,Xi, Yukun,Huang, Zhibin,Shi, Daqing
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p. 13645 - 13653
(2014/01/06)
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- Continuous-flow microliter microwave irradiation in the synthesis of isoxazole derivatives: An optimization procedure
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An efficient method was developed for the synthesis of 3,4,5-trisubstituted and 3,5-disubstituted isoxazoles by using continuous-flow microwave-heated microreactors. A study on the separate effects of the temperature, continuous-flow regime, and microwave irradiation showed that the continuous-flow regime had important effects for less reactive diketones, where microwave heating enhanced the reaction, permitting the formation of 5-methyl-3-phenylisoxazole, which was not formed in the absence of microwaves. Georg Thieme Verlag Stuttgart · New York.
- Rodriguez, Antoniom.,Juan, Alberto,Gomez, M.Victoria,Moreno, Andres,De La Hoz, Antonio
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experimental part
p. 2527 - 2530
(2012/08/29)
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- Copper induced cyclization of α,β-unsaturated carbonyl compounds to isoxazoles
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An unusual synthesis of isoxazoles from α,β-unsaturated ketoximes is reported. Using very inexpensive reagents, isoxazoles are isolated in good yields. Notably, a mixture of E and Z oxime isomers is employed. Initial studies indicate the oxidative cyclization reaction does not proceed via radical route; a copper insertion/elimation route is proposed.
- Browder, Cindy C.,Moss, Christopher B.,Kraft, Matthew B.,Petrucka, Paige L.,Morey, Tara S.,Leach, Christopher W.,Gearhart, Nicholas C.
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scheme or table
p. 229 - 233
(2012/05/19)
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- Photolysis of (3-methyl-2H-azirin-2-yl)-phenylmethanone: Direct detection of a triplet vinylnitrene intermediate
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The photoreactivity of (3-methyl-2H-azirin-2-yl)-phenylmethanone, 1, is wavelength-dependent (Singh et al. J. Am. Chem. Soc. 1972, 94, 1199-1206). Irradiation at short wavelengths yields 2P, whereas longer wavelengths produce 3P. Laser flash photolysis of
- Rajam, Sridhar,Murthy, Rajesh S.,Jadhav, Abhijit V.,Li, Qian,Keller, Christopher,Carra, Claudio,Pace, Tamara C.S.,Bohne, Cornelia,Ault, Bruce S.,Gudmundsdottir, Anna D.
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supporting information; experimental part
p. 9934 - 9945
(2012/02/03)
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- Condensed oxaziridine-mediated [3+2] cycloaddition: Synthesis of polyhetero-bicyclo compounds
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Polyhetero-bicyclo compounds were synthesized by a regioselective [3+2]-cycloaddition reaction between stable condensed oxaziridines and alkenes, alkynes, and nitriles. These molecules showed considerable antimicrobial activity against several gram-positive bacteria.
- Videtta, Valeria,Perrone, Serena,Rosato, Francesca,Alifano, Pietro,Tredici, Salvatore M.,Troisi, Luigino
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scheme or table
p. 2781 - 2783
(2010/12/25)
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- Gold(III)-catalyzed synthesis of isoxazoles by cycloisomerization of α,β-acetylenic oximes
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Cycloisomerization of,-acetylenic oximes leading to substituted isoxazoles was achieved using AuCl3 as catalyst, under moderate reaction conditions. The reaction can be applied to various acetylenic oximes and gives good to excellent yields. Th
- Praveen,Kalyanasundaram,Perumal
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experimental part
p. 777 - 781
(2010/06/12)
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- Synthesis of isochalcogenazole rings by treating β-(N,N- dimethylcarbamoylchalcogenenyl)alkenyl ketones with hydroxylamine-O-sulfonic acid
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β-(N,N-Dimethylcarbamoylselenenyl)- and β-(N,N- dimethylcarbamoyltellurenyl)alkenyl ketones were converted into isoselenazoles and isotellurazole Te-oxides, respectively, simply by treating with hydroxylamine-O-sulfonic acid, and deoxygenation of the latt
- Shimada, Kazuaki,Moro-oka, Akiko,Maruyama, Akiko,Fujisawa, Hiroyuki,Saito, Toshio,Kawamura, Ryo,Kogawa, Hisashi,Sakuraba, Maiko,Takata, Yukichi,Aoyagi, Shigenobu,Takikawa, Yuji,Kabuto, Chizuko
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p. 567 - 577
(2008/02/11)
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- Reactions of lithium silylcuprates with pyrazolium and indazolium salts
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Although pyrazolium salts have been shown to be unreactive toward lithium carbocuprates, these substrates were opened by lithium silylcuprate reagents to give versatile N-silylated β-enaminoimines stabilized by coordination of the silyl group with both ni
- Gonzalez-Nogal, Ana M.,Calle, Mariola,Cuadrado, Purificacion
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p. 6089 - 6096
(2008/09/17)
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- Dioximes of 1,3-diketones in the trofimov reaction: New 3-substituted pyrroles
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Dioximes of 1,3-diketones enter into the Trofimov reaction forming pyrroles containing an acyl or an O-vinyloxime substituent in position 3 of the pyrrole. In the case of sterically hindered dioximes the main reaction products are isoxazoles. 2005 Springer Science+Business Media, Inc.
- Zaitsev,Schmidt,Mikhaleva,Afonin,Ushakov
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p. 722 - 729
(2007/10/03)
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- Catalytic effect of wet molecular sieve 3A in dry media on syntheses of oximes and 1,3-dioximes
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A simple, efficient and eco-friendly method has been developed for the condensation of hydroxylamine hydrochloride with aldehydes, ketones and 1,3-diketones in the presence of powdered molecular sieves (3A) as catalyst. Aldoximes, ketoximes and 1,3-dioximes were obtained in excellent yields.
- Bigdeli, Mohammadali,Rahmati, Abbas
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p. 605 - 607
(2007/10/03)
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- Nitrile oxide cycloaddition chemistry using benzotriazole as a steric auxiliary
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The relatively hindered 2,2-bis(benzotriazol-1-yl)acetonitrile oxide was prepared in situ from the precursor hydroximinoyl chloride, and was allowed to react with dipolarophiles to give rise to several isoxazoles. The benzotriazole substituents acted as s
- Savage, G. Paul,Wernert, Gregory T.
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p. 877 - 881
(2007/10/03)
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- Domino primary alcohol oxidation-wittig reaction: Total synthesis of ABT-418 and (E)-4-oxonon-2-enoic acid
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Domino oxidation of primary alcohols to α,β-unsaturated compounds using the combination of PCC-NaOAc and stabilized Wittig reagent and its application towards total synthesis of ABT-418 and 4-oxonon-2-enoic acid is described.
- Shet, Jyoti,Desai, Vidya,Tilve, Santosh
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p. 1859 - 1863
(2007/10/03)
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- A method for generating nitrile oxides from nitroalkanes: A microwave assisted route for isoxazoles
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A convenient route has been developed for generation of nitrile oxides in situ from nitroalkanes under very mild conditions using microwave irradiation, using 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) and DMAP as catalyst.
- Giacomelli, Giampaolo,De Luca, Lidia,Porcheddu, Andrea
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p. 5437 - 5440
(2007/10/03)
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- Structural Investigation of 3,5-Disubstituted Isoxazoles by 1H-Nuclear Magnetic Resonance
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HIV-1 integrase (IN) is a very promising and validated target for the development of therapeutic agents against AIDS. In an effort to design and synthesize biological isosteric analogs of β-diketoacid-containing inhibitors of IN, we prepared a series of s
- Sechi, Mario,Sannia, Luciano,Orecchioni, Maria,Carta, Fabrizio,Paglietti, Giuseppe,Neamati, Nouri
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p. 1097 - 1102
(2007/10/03)
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- An efficient, scaleable procedure for the conversion of esters to isoxazoles
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A concise, regiocontrolled route to isoxazoles, based on the condensation of an ester with a metallated imine, has been developed. The intermediate vinylogous amides react smoothly with hydroxylamine to provide, after dehydration, substituted isoxazoles. The method has been used for the multi-kilo scale preparation of ABT-418, a novel cholinergic channel activator.
- Bunnelle,Singam,Narayanan,Bradshaw,Liou
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p. 439 - 442
(2007/10/03)
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- Generation of Nitrile Oxides via O-Tributylstannyl Aldoximes; Application to the Synthesis of Isoxazolines and Isoxazoles
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Nitrile oxides were generated readily by the reaction of aldoximes 1, with tert-butyl hypochlorite and bis(tributyltin) oxide.The reaction proceeded efficiently under mild conditions, in which O-stannylated aldoximes 2 are thought to be key intermediates.This reaction system was applicable to the one-pot syntheses of isoxazole derivatives 4 and 5 in the presence of dipolarophiles via a cycloaddition.
- Moriya, Osamu,Takenaka, Hideo,Iyoda, Masaichi,Urata, Yoshikiyo,Endo, Takeshi
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p. 413 - 418
(2007/10/02)
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- 1,3-Dipolar cycloaddition reaction of substituted trimethylstannylacetylenes with nitrile oxides
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1,3-Dipolar cycloaddition reaction of trimethylstannylacetylene with nitrile oxides yielded 3-substituted 5-(trimethylstannyl)isoxazoles. On the other hand, the same reaction of (trimethylstannyl)phenylacetylene, -1-hexyne, and -(trimethylsilyl)acetylene
- Sakamoto,Uchiyama,Kondo,Yamanaka
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p. 478 - 480
(2007/10/02)
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- Synthesis of 3-Substituted 5-Arylisoxazoles from α,β-Unsaturated Oximes
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The synthesis of 3-substituted 5-arylisoxazoles from oximes of α,β-unsaturated ketones is studied. The formation of the isoxazole derivatives takes place by cyclization of oximes in the presence of iodine and potassium iodide. The presence of isoxazoline
- Alberola, Angel,Banez, J. Manuel,Calvo, Luis,Rodriguez, M. Teresa Rodriguez,Sanudo, M. Carmen
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p. 467 - 471
(2007/10/02)
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- SYNTHESIS OF ISOXAZOLE DERIVATIVES IN REACTION OF 2-HYDROXYPHENYLCARBONYL COMPOUNDS OR 1,3-DIKETONES WITH HYDROXYLAMINE-O-SULFONIC ACID
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2-Hydroxybenzaldehyde 1a and 2-hydroxyacetophenone 1b react with hydroxylamine-O-sulfonic acid (HSA) yielding the corresponding oxime hydrogensulfates 2a and 2b, separated as potassium salts.These salts undergo conversion with good yields to benzisoxazole 3a and 2-methylbenzoxazole 3b, respectively.In similar reaction of 1,3-diketones, both cyclic and acyclic 1c-k with HSA, isoxazole derivatives 3c-k were obtained.
- Suwinski, J.,Walczak, K.
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p. 777 - 785
(2007/10/02)
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- Synthesis of Isoxazolines and Isoxazoles via Generation of Nitrile Oxides from O-Stannyl Aldoximes
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The reactions of O-tributylstannyl aldoximes and active halogen compounds such as tert-butyl hypochlorite or N-bromosuccinimide, whereby nitrile oxides are generated effectively, are applied to the preparations of isoxazolines and isoxazoles via d
- Moriya, Osamu,Takenaka, Hideo,Urata, Yoshikiyo,Endo, Takeshi
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p. 1671 - 1672
(2007/10/02)
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- Condensed heteroaromatic ring systems. XIX. Synthesis and reactions of 5-(tributylstannyl)isoxazoles
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3-Substituted 5-(tributylstannyl)isoxazoles were newly synthesized by the 1,3-dipolar cyctoadditton of nitrile oxides to tributylethynylstannane. The iodination and the palladium-catalyzed benzoylation of 5-(tributylstannyl)-3-methylisoxazolegave 5-iodo-3-methylisoxazole and 3-methyl-5-isoxazolyl phenyl ketone in satisfactory yields, respectively. The palladium-catalyzed cross-coupling reaction of the stannylisoxazole with 2-bromonitrobenzene followed by the catalytic hydrogenation over Raney nickel resulted in the formation of 2-methyll-4(1H)-quinolinone in 57% overall yield.
- Sakamoto, Takao,Kondo, Yoshinori,Uchiyama, Daishi,Yamanaka, Hiroshi
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p. 5111 - 5118
(2007/10/02)
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- A Regioselective Synthesis of 3,5-Disubstituted Isoxazoles
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The 3-aryl-5-, and 5-aryl-3-(phenylsulphonylmethyl)isoxazoles (6) and(9) respectively were regioselectively prepared from 1-aryl-3-methylthio-4-phenylsulphonylbut-2-en-1-one (1).As an application of the present method, 3-methyl-5-(4-.pyridyl)isoxazole (2)
- Yokoyama, Masataka,Tsuji, Kouichi,Kushida, Mari
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- RING TRANSFORMATION REACTION OF 1,4,6-TRISUBSTITUTED 2(1H)-PYRIMIDINONES AND -THIONES WITH HYDROXYLAMINE
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1,4,6-Trisubstituted 2(1H)-pyrimidinones (Ia-e) underwent ring transformation with hydroxylamine to afford 3,5-disubstituted isoxazoles (IIa-e) in high yields.On the other hand, 2(1H)-pyrimidinethiones (IIIa, b, f-k) underwent ring transformation to give mainly a new type of N-substituted 2-aminopyrimidine 1-oxides (IVa, b, f-k) as well as isoxazoles.The reaction of pyrimidinium salts (VII, VIII, and IX) with hydroxylamine is also discussed.Keywords: - ring tranformation reaction; hydroxylamine; nucleophilic reaction; 3,5-disubstituted isoxazoles; N-substituted 2-aminopyrimidine 1-oxides; pyrimidinium salts
- Kashima, Choji,Katoh, Akira,Yokota, Yuko,Omote, Yoshimori
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p. 2516 - 2519
(2007/10/02)
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- Halogenation of Vinyl Ketoximes. Synthesis of Isoxazoles and Preparation and Silver Ion-Promoted Reactions of 4-Halo-2-isoxazolines
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Reaction of several α,β-unsaturated ketoximes with N-bromosuccinimide (NBS) gave isoxazoles, but yields were lower and the reaction less general than a similar transformation using iodine under basic conditions.With β,β-disubstituted oximes, 4-halo-5,5-disubstituted-2-isoxazolines were obtained using NBS, iodine, or N-chlorosuccinimide.Treatment of the 4-bromoisoxazolines with silver acetate or silver nitrate caused either elimination with rearrangement to give isoxazoles or substitution at C-4, depending upon the nature of the substituents at C-5.
- Hansen, John F.,Kim, Yong In,McCrotty, Stephen E.,Strong, Scott A.,Zimmer, Douglas E.
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p. 475 - 479
(2007/10/02)
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- SYNTHESIS OF HETEROCYCLES: PART I. N-IODOSUCCINIMIDE, A CONVENIENT OXITATIVE CYCLISING AGENT IN THE SYNTHESIS OF OXAZOLE, ISOXAZOLE, BENZOFURAN, FUROXAN AND 1,2,3-TRIAZOLE-1-OXIDE DERIVATIVES
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N-Iodosuccinimide has been successfully employed as an oxidative cyclising agent for the synthesis of oxazole, isoxazole, benzofuran, furoxan and 1,2,3-triazole-1-oxide derivatives.Synthesis of compounds (II), (IV), (VI), (VIII) and (X) having these basic skeletons respectively are reported.
- Talapatra, Sunil K.,Chaudhuri, Prabir,Talapatra, Bani
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p. 1279 - 1282
(2007/10/02)
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