1008-75-9Relevant articles and documents
Efficient and convenient method for the synthesis of isoxazoles in ionic liquid
Valizadeh, Hassan,Amiri, Mohammad,Gholipur, Hamid
, p. 108 - 110 (2009)
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
Convenient synthesis of 3,5-disubstituted isoxazoles
Kurangi, Reshma F.,Kawthankar, Rima,Sawal, Sulfala,Desai, Vidya G.,Tilve, Santosh G.
, p. 587 - 589 (2007)
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.
SYNTHESIS AND REACTIONS OF 5-(TRIBUTYLSTANNYL)ISOXAZOLES
Kondo, Yoshinori,Uchiyama, Daishi,Sakamoto, Takao,Yamanaka, Hiroshi
, p. 4249 - 4250 (1989)
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
An improved method for preparation of nitrile oxides from nitroalkanes for in situ dipolar cycloadditions
Basel, Yochai,Hassner, Alfred
, p. 309 - 312 (1997)
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
Reactivity of p-phenyl substituted β-enamino compounds using k- 10/ultrasound. II [1]. Synthesis of isoxazoles and 5-isoxazolones
Valduga, Claudete J.,Santis, Denise B.,Braibante, Hugo S.,Braibante, Mara E. F.
, p. 505 - 508 (1999)
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.
A photochemical one-pot three-component synthesis of tetrasubstituted imidazoles
Pusch, Stefan,Opatz, Till
, p. 5430 - 5433 (2014)
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)
Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles
Baglieri, Ausilia,Meschisi, Luca,De Sarlo, Francesco,Machetti, Fabrizio
, p. 4643 - 4655 (2016)
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.
NH2OH-HCl-Mediated Umpolung α-Methylsulfonylation of α-Sulfonyl Ketones with Methylsulfoxides: Synthesis of α,β-Bis-sulfonyl Arylketones
Chang, Meng-Yang,Chen, Han-Yu,Tsai, Yu-Lin
, p. 1832 - 1836 (2019)
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.
NHC-palladium-catalyzed ionic liquid-accelerated regioselective oxyarylation of alkynes with diaryl ethers?
Cen, Liying,He, Dan,Jiang, Huanfeng,Li, Jianxiao,Lin, Zidong,Wu, Wanqing
supporting information, p. 1983 - 1988 (2022/04/03)
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.
AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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Page/Page column 58-59, (2020/06/10)
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.