Category: 5765-44-6

Proton spin-spin coupling constants in isothiazole, isoxazole, and some of their alkyl derivatives was written by Wasylishen, Roderick E.;Rowbotham, J. Brian;Schaefer, Ted. And the article was included in Canadian Journal of Chemistry in 1974.Computed Properties of C4H5NO This article mentions the following:

The signs and magnitudes of the spin-spin coupling constants over three to six bonds between protons in isothiazole, isoxazole, and in 10 of their alkyl derivatives are discussed in terms of the coupling mechanisms. The chem. shifts of ring protons and Me protons arise from a common mechanism originating in the ring but are not simply related to electron ds. calculated by MO theory at the CNDO/2 level of approximation In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Computed Properties of C4H5NO).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. The weakness of this bond allows the ring opening of these heterocycles under reductive conditions. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Computed Properties of C4H5NO

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Preparation of β-oxo nitriles through acylation of trimethylsilyl cyanoacetate by mixed anhydrides was written by Goasdoue, Claude;Couffignal, Rene. And the article was included in Tetrahedron Letters in 1979.SDS of cas: 5765-44-6 This article mentions the following:

Treating Me₃SiO₂CCHLiCN (I) and EtCHLiCN with RCO₂CO₂Et (R = Pr, Ph) gave 59 and 74% RCOCH₂CN, and 55 and 74% RCOCHEtCN, resp. I was prepared by treating HO₂CCH₂CN with Me₃SiCl (90%) followed by lithiation. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6SDS of cas: 5765-44-6).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter. Isoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.SDS of cas: 5765-44-6

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

β-Aminovinyl ketones. II. Some reactions of alkyl 2-dialkylaminovinyl ketones was written by Kochetkov, N. K.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1954.Safety of 5-Methylisoxazole This article mentions the following:

AcCH:CHNEt₂ (I) (5 g.) in 40 ml. EtOH hydrogenated over 0.15 g. PtO₂ 11 hrs. at room temperature absorbed only 750 ml. H; distillation gave 2.1 g. original I, along with a fraction, b. below 85°; acidification of the latter with HCl and redistillation gave a distillate in which AcEt was detected, while the distillation residue contained Et₂NH.HCl. Thus ketones of this type are hydrogenolyzed readily. Heating 14 g. I and 7.5 g. NH₂OH.HCl in 40 ml. MeOH 5 hrs., then adding 70 g. CdCl₂ in 50 ml. H₂O gave a crop of crystals, which were separated, moistened with a little H₂O, and subjected to dry distillation, yielding 59% 5-methylisoxazole, b₇₅₀ 121-2°, d₂₀ 1.0224, n_D²⁰ 1.4368; this treated with EtONa in EtOH, then with Et₂O, gave a precipitate of Na salt of AcCH₂CN, corresponding to 92% yield; this readily gave MeC(:NNPh)CH₂CN, m. 100-1°. Heating 13 g. PrCOCH:CHNMe₂ with 7.5 g. NH₂OH.HCl in MeOH as above 5 hrs., adding 3 volumes H₂O, and extracting with Et₂O gave 89% 5-propylisoxazole, b. 161-1.5°, d₂₀ 0.9682, n_D²⁰ 1.4460; with EtONa-EtOH this gave 91.4% Na salt or PrCOCH₂CN; phenylhydrazone of the ketone, m. 96°. AcCH:CHNMe₂ (5 g.) and 4.5 g. NCCH₂CONH₂ in 50 ml. H₂O refluxed 2 hrs., the mixture cooled, filtered, and the filtrate heated 2 hrs. longer gave 65% (total) 2-hydroxy-3-cyano-6-methylpyridine, m. 278-80°; a 59% yield is obtained when the amino ketone is prepared in situ by treating AcCH:CHCl with aqueous Me₂NH and then following the above procedure. Similarly PrCOCH:CHNMe₂ and NCCH₂CONH₂ gave in 5 hrs. 72% 2-hydroxy-3-cyano-6-propylpyridine, m. 147-8°, while iso-BuCOCH:CHNMe₂ gave 74.8 % 6-iso-Bu homolog, m. 148-9° (from EtOH). To MeMgI from 47 g. MeI in 250 ml. Et₂O was added with good cooling 41 g. AcCH:CHNMe₂, yielding an oil which soon solidified; the mixture was treated after 3 hrs. with 10% HCl and extracted with Et₂O yielding 19.8% AcCH:CHMe, b. 121-3°, d₂₀ 0.8573, n_D²⁰ 1.4390; 2,4-dinitrophenylhydrazone, m. 153-4°. Refluxing 25 g. AcCH:CHNMe₂ and 52 g. MeI 6 hrs., cooling, adding 50 ml. H₂O, heating 0.5 hr., steam distilling the MeI, extracting with Et₂O, and distilling the extract gave 17.5% AcCMe:CHOH, b. 145-8°, m. 72°. AcCH:CHNMe₂ (6 g.) and 9 g. MeI in C₆H₆ refluxed 4 hrs. and the mixture allowed to stand several days gave 33% of a crystalline addition product, C₇H₁₄ONI, decompose 120-2°, yielding with hot H₂O AcCMe:CHOH, identical with the above specimen. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Safety of 5-Methylisoxazole).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazoles present in various natural products and synthetic compounds of biological importance like antibacterial, antagonists, antiinflammatory, analgesics, and also show the applications in functional materials. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Safety of 5-Methylisoxazole

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Synthesis, Biological Evaluation, and Structure-Activity Relationships for 5-[(E)-2-Arylethenyl]-3-isoxazolecarboxylic Acid Alkyl Ester Derivatives as Valuable Antitubercular Chemotypes was written by Pieroni, Marco;Lilienkampf, Annamaria;Wan, Baojie;Wang, Yuehong;Franzblau, Scott G.;Kozikowski, Alan P.. And the article was included in Journal of Medicinal Chemistry in 2009.Synthetic Route of C4H5NO This article mentions the following:

Tuberculosis (TB), mostly caused by Mycobacterium tuberculosis (Mtb), is one of the leading causes of death from infectious disease worldwide. Its coinfection with HIV and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains have further worsened the TB pandemic. Despite its global impact, TB is considered a neglected disease and no new anti-TB therapeutics have been introduced over the last four decades. The nonreplicating persistent form of TB (NRP-TB) is responsible for the length of the treatment and is the putative cause of treatment failure. Therefore, new anti-TB agents, which are active against both the replicating form of Mtb (R-TB) and NRP-TB, are urgently needed. The synthesis and structure-activity relationships (SAR) of a series of 5-[(E)-2-arylethenyl]-3-isoxazolecarboxylic acid alkyl esters e.g. I, as potent anti-TB agents are reported. Several compounds had submicromolar min. inhibitory concentrations (MIC) against R-TB and were active against NRP-TB in the low micromolar range, thus representing attractive lead compounds for the possible development of new anti-TB agents. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Synthetic Route of C4H5NO).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter. Isoxazoles are potent isosteres of pyridine and have been found to inhibit voltage-gated sodium channels for pain control, for the construction of tetracycline antibiotic derivatives, and as a therapeutic agent for depression.Synthetic Route of C4H5NO

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Preparation and reactivity of acetoacetonitrile dianion was written by Vinick, Fredric J.;Pan, Yolanda;Gschwend, Heinz W.. And the article was included in Tetrahedron Letters in 1978.Application In Synthesis of 5-Methylisoxazole This article mentions the following:

The title dianion (I) was prepared by treating 5-methylisoxazole (II) with 2 equiv LiN(CHMe₂)₂ in THF at -10°. I underwent alkylation by alkyl halides RX to give unstable RCH₂COCH₂CN; immediate NaBH₄ reduction of the products gave RCH₂CH(OH)CH₂CN (R = allyl, Pr, PhCH₂) in 49-52% overall yield from II. I with RCOR¹ (R = H, R¹ = 4-ClC₆H₄; R = R¹ = Ph) gave 44-82% RC(OH)R¹CH₂CH(OH)CH₂CN. I with PhCN gave 24% PhC(NH₂):CHCOCH₂CN. I with RC₆H₄CN (R = 4-MeO, -Cl, 3-Me) gave 62-5% of the corresponding 6-(RC₆H₄)-substituted 2-amino-4(1H)-pyridones. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Application In Synthesis of 5-Methylisoxazole).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. The most common methods for N–O bond cleavage in isoxazoles are hydrogenation with palladium or platinum catalysts or with Raney Ni. Recent developments have shown that Mo(CO)6 efficiently cleaves the N–O bond in isoxazoles.Application In Synthesis of 5-Methylisoxazole

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

β-Methylisoxazole was written by Pino, Piero;Ercoli, Raffaele. And the article was included in Rend. ist. lombardo sci, Pt. I, Classe sci. mat. e nat. in 1955.Product Details of 5765-44-6 This article mentions the following:

The chemical behavior of β-methylisoxazole (I) is similar to that of the α-isomer (II). I is somewhat more stable towards halogenation but is less stable towards alkali than II or the γ-isomer (III) but is more stable than isoxazole. Ring opening occurs by the same mechanism as for I (C.A. 49, 6228i). The following rate constants for the ring opening reaction are (compound and k × 10⁴ l. mole^-1 sec.^-1 given). I 3.1, II 1.4, III 0.1, IV 4.5. Thus from I and β-phenylisoxazole can be prepared NCCHMeCHO and NCCHPhCHO, resp. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Product Details of 5765-44-6).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter. Fe(CO)5 efficiently cleaves the N–O bond of fused isoxazolo-1,4-quinones to give the corresponding imines.All the common reducing reagents failed to open the isoxazole ring.Product Details of 5765-44-6

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

A mass spectrometric labeling strategy for high-throughput reaction evaluation and optimization: exploring C-H activation was written by Szewczyk, Jason W.;Zuckerman, Rebecca L.;Bergman, Robert G.;Ellman, Jonathan A.. And the article was included in Angewandte Chemie, International Edition in 2001.Computed Properties of C4H5NO This article mentions the following:

Mass spectrometric labeling with H₂NO-Gly-(Arg)₄-OH (I) was used for pos. ion ESI-MS evaluation of high throughput reactions. A mixture of a heteroaromatic compound and neohexene was subjected to C-H activation with [Ru₃(CO)₁₂] and CO. The products were then converted to their oximes with I, effectively silencing remaining starting materials and decomposition products and allowing the desired products to be determined directly by pos. ion ESI-MS. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Computed Properties of C4H5NO).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazole rings are found in some natural products, such as ibotenic acid and muscimol. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Computed Properties of C4H5NO

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Tandem mass spectrometry study of the flash vacuum pyrolysis of some 1,2,4-triazolides was written by Maquestiau, A.;Puk, E.;Flammang, R.. And the article was included in Bulletin des Societes Chimiques Belges in 1987.Product Details of 5765-44-6 This article mentions the following:

A real-time anal. of the flash-vacuum pyrolysis products of 1,2,4-triazolides was performed by tandem mass spectrometry. Thus, 1-acyltriazoles gave 5-alkyloxazoles, in competition with formation of ketenes. This ring formation occurred by a sigmatropic shift of the acyl group from N to C, loss of N, and cyclization of the biradical intermediate. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Product Details of 5765-44-6).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter. The electrophilic cyclization of various 2-alkynone O-methyl oximes with a wide range of substrates such as ICl, I2, Br2, PhSeBr, etc. provides a variety of 3,4,5-trisubstituted isoxazoles in good to excellent yields.Product Details of 5765-44-6

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The pyrolysis of isoxazole revisited: A new primary product and the pivotal role of the vinylnitrene. A low-temperature matrix isolation and computational study was written by Nunes, Claudio M.;Reva, Igor;Pinho e Melo, Teresa M. V. D.;Fausto, Rui;Solomek, Tomas;Bally, Thomas. And the article was included in Journal of the American Chemical Society in 2011.Quality Control of 5-Methylisoxazole This article mentions the following:

This paper describes the pyrolysis of parent isoxazole and of its 5-Me and 3,5-di-Me derivatives by the high-pressure pulsed pyrolysis method, where activation of the precursor mols. occurs predominantly by collisions with the host gas (Ar in our case), rather than with the walls of the pyrolysis tube, where catalyzed processes may occur. The products were trapped at 15 K in Ar matrixes and were characterized by vibrational spectroscopy. Thereby, hitherto unobserved primary products of pyrolysis of isoxazole and of its 5-Me derivative, 3-hydroxypropenenitrile or 3-hydroxybutenenitrile, resp., were observed E-Z photoisomerization could be induced in the above hydroxynitriles. On pyrolysis of isoxazole, ketenimine and CO were observed as decomposition products, but this process did not occur when the 5-Me derivative was pyrolyzed. Instead, the corresponding ketonitrile was formed. In the case of 3,5-dimethylisoxazole, 2-acetyl-3-methyl-2H-azirine was detected at moderate pyrolysis temperatures, whereas at higher temperatures, 2,5-dimethyloxazole was the only observed rearrangement product (next to products of dissociation). These findings are rationalized on the basis of quantum chem. calculations Thereby it becomes evident that carbonyl-vinylnitrenes play a pivotal role in the observed rearrangements, a role that had not been recognized in previous theor. studies because it had been assumed that vinylnitrenes are closed-shell singlet species, whereas they are in fact open-shell singlet biradicaloids. Thus, the primary processes had to be modeled by the multiconfigurational CASSCF method, followed by single-point MR-CISD calculations The picture that emerges from these calculations is in excellent accord with the exptl. findings; i.e., they explain why some possible products are observed while others are not. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Quality Control of 5-Methylisoxazole).

5-Methylisoxazole (cas: 5765-44-6) belongs to isoxazole derivatives. Isoxazole are described as inhibitors of acetylcholinesterase (AChE). Isoxazole ligands bind to and inhibit the Sxc- antiporter. Some alternative routes for the synthesis of isoxazoles have also been developed and reported. The 2-benzoyl-2-halo-2H-azirines provide 4-haloisoxazoles in good yields after heating in toluene at reflux temperature.Quality Control of 5-Methylisoxazole

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem