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1008-75-9, Name is 3-Methyl-5-phenylisoxazole, belongs to isoxazole compound, is a common compound. Safety of 3-Methyl-5-phenylisoxazoleIn an article, once mentioned the new application about 1008-75-9.

A comparative study of reactions of 3-methyl-5-phenylisoxazole and 3-methyl-5-phenylisothiazole with electrophilic compounds in the presence of n-BuLi, LICA or LICA-TMEDA is reported.By using LICA-TMEDA, regioselective reactions of heterocyclic compounds at the C-3 methyl group are obtained.With n-BuLi or LICA and the isoxazole derivative a product mixture at the C-4 position and the C-3 methyl group is found.In the case of isothiazole compound, only with methyl iodide and n-BuLi, the dialkylated product at both positions is formed.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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1008-75-9, Name is 3-Methyl-5-phenylisoxazole, belongs to isoxazole compound, is a common compound. Safety of 3-Methyl-5-phenylisoxazoleIn an article, once mentioned the new application about 1008-75-9.

4-rylisoxazoles can be easily prepared by a palladium-catalysed C-H bond activation/arylation of 3,5-disubstituted isoxazoles using aryl or heteroaryl bromides. Good yields were generally obtained by using 0.1-0.5 mol-% of the airstable PdCl2 complex as the catalyst. A range of functional groups such as acetyl, formyl, ester, fluoro, nitro, trifluoro-methyl or nitrile on the aryl bromide is tolerated. This reaction is environmentally attractive, as the major waste is KBr/ AcOH instead of the metallic salts arising from classical cross-coupling procedures,

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Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Put a nickel in it: Azaarylacetates and acetamides, which have been neglected as substrates in catalytic asymmetric synthesis, undergo highly enantioselective Michael additions to nitroalkenes in the presence of a chiral nickel(II)-bis(diamine) complex (see scheme; Bn=benzyl, MS=molecular sieves). This process is tolerant of a wide variety of azaarenes in the pronucleophile. Copyright

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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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 beta-diketoacid-containing inhibitors of IN, we prepared a series of substituted isoxazole carboxylic acids. Several of these compounds inhibited catalytic activities of purified IN at micromolar concentration range. With an aim to prepare a large number of analogues based on the isoxazole pharmacophore we focused our study on a series of 3,5-disubstituted isoxazole isomers. For a rapid structural analysis we discovered a convenient 1H-nmr method for distinguishing between isomeric structures based on their H-4 assignments. This “finger print” approach to isomer identification will be useful in combinatorial chemistry settings where a mixture can be further derivatized.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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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 beta-enaminoimines stabilized by coordination of the silyl group with both nitrogen atoms. In contrast, the behaviour of indazolium salts on treatment with the same reagents is more complex. Depending on the substitution patterns of the indazolium salts, the nature of the silylcuprate and even on the temperature, we obtained 3-silylindazolines and other interesting products resulting either from the opening of the heterocyclic ring or from modification by its opening/closing. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Tetrasubstituted imidazoles can be formed in a photochemical one-pot synthesis from aldehydes, alpha-aminonitriles, and isoxazoles. Condensation of the first two components produces alpha-(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)

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Phosphonium salts 2 and 6, upon deprotonation with BuLi and subsequent reaction with acyl halides, yield the gamma-acyl derivatives 3 and 7, respectively, which on treatment with hydrochloric acid afford the corresponding (dioxoalkyl)phosphonium salts 4 and 8.Isoxazole derivatives 9 and 10 are formed regioselectivly from 4 and 8 with NH2OH*HCl, while with R-NH-NH2*HCl (R = H or C6H5) the pyrazole-containing phosphonium salts 14 and 15 are obtained in an analogous reaction.In each case the direction of cyclisation is different to the reactions of the corresponding non-phosphorus substituted 1,3-dioxo compounds.On treatment with aqueous NaOH 9 and 10 are cleaved to triphenylphosphane oxide and isoxazoles 11 and 12, while 14 and 15 yield the pyrazoles 16 and 17.Wittig reaction of 9a or 14a with aldehydes or ketones leads to the isoxazole olefins 13 or the pyrazole olefins 18, respectively.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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1008-75-9, Name is 3-Methyl-5-phenylisoxazole, belongs to isoxazole compound, is a common compound. name: 3-Methyl-5-phenylisoxazoleIn an article, once mentioned the new application about 1008-75-9.

In the presence of hexacarbonylmolybdenum, substituted isoxazoles undergo a cycloaddition reaction with dimethyl acetylenedicarboxylate across the C-4-C-5 bond to give 3,4-bis(methoxycarbonyl)pyridine derivatives.In a similar cycloadition of isoxazoles with methyl propiolate, 4-(methoxycarbonyl)pyridine derivatives were also obtained.The beta-carbon atom of methyl propiolate could intervene in the bonding with the C-5 position of the isoxazoles regioselectively.A mechanism involving a complexed 2-oxa-3-azabicyclo<3.2.0>hepta-3,6-diene derivative and the subsequent N-Oand C-1-C-5 bond cleavage leading to a complexed (beta-ketovinyl)nitrene intermediate is proposed for the formation of pyridine derivatives.In order to clarify the mechanistic aspect, the reaction of 4-phenyl-2-oxa-3-azabicyclo<3.2.0>hepta-3,6-diene and its related compounds were also studied to give pyridine derivatives.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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A synthesis of highly substituted 2,4-diacylpyrroles through a Cu-catalyzed dimerization of acylazirines generated in situ by a photochemical valence isomerization is described. The shown methodology allows the use of simple precursors and a readily available copper(II)-catalyst. Since the reaction is best performed at elevated temperatures, a method to adjust the temperature of the reaction mixture during this dual light and metal-induced process was established. Additionally, mechanistic studies of the reaction were performed in order to provide a deeper understanding of the chemistry of 2-acylazirines.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

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Some isoxazoles, isoxazolines, and their quaternized derivatives have been investigated by polarography and preparative reduction.A reductive cleavage of the oxygen-nitrogen bond without reduction of the carbon-nitrogen double bond was possible in protic medium for the quaternized derivatives, whereas for the parent compounds this was possible only in aprotic medium.By this means, preferentially via quaternization, isoxazoles and isoxazolines may be transformed to beta-diketones or beta-hydroxyketones.Under suitable conditions, the quaternized isoxazoles and isoxazolines may be reduced to 1,3-aminoalcohols, the erythro:threo ratio of the products differing considerably.

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Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem