Day: October 13, 2022

In 1970,Tetrahedron included an article by Wamhoff, Heinrich. HPLC of Formula: 29278-09-9. The article was titled 《Heterocyclic β-enamino esters. III. NMR spectroscopic study of the protonation of heterocyclic β-enamino esters》. The information in the text is summarized as follows:

Partially hydrogenated heterocyclic β-enamino esters of the 4,5-dihydrofuran, -thiophene, 5,6-dihydro-4H-pyran and -thiopyran type are protonated in trifluoroacetic acid at position 3 (Cβ-protonation). The course and place of this protonation was studied by means of NMR spectroscopy and the results compared with protonation experiments carried out on unsaturated N-containing heterocyclics of this type. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9HPLC of Formula: 29278-09-9)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.HPLC of Formula: 29278-09-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

《Heterocyclic β-enamino esters. 48. Heterocondensed pyridines by cycloaddition-extrusion sequence of bi- and tricyclic 1,3-oxazinones with N,N-diethyl-1-propynylamine》 was published in Chemische Berichte in 1987. These research results belong to Ming, Yangfu; Horlemann, Norbert; Wamhoff, Heinrich. HPLC of Formula: 29278-09-9 The article mentions the following:

Heterocondensed pyridines, e.g. I (R = CHMe2, Ph), were prepared from the corresponding heterocondensed 1,3-oxazinones, e.g. II, and MeCCNEt2 via a regiospecific cycloaddition-extrusion sequence. 4H-Furo[2,3-d]-1,3-oxazin-4-one III, one of the 1,3-oxazinones which underwent the above reaction to give the appropriate heterocondensed pyridine, was prepared by cyclizing dihydrofuran IV by Br2PPh3. 1,3-Oxazinones V and VI were prepared similarly.Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9HPLC of Formula: 29278-09-9) was used in this study.

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.HPLC of Formula: 29278-09-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

《Syntheses of nitrogen-containing heterocycles. XXI. The preparation and reactions of some isoxazoles》 was published in Chemische Berichte in 1960. These research results belong to Dornow, Alfred; Treckenburg, Harald. SDS of cas: 29278-09-9 The article mentions the following:

The reaction of the enol ethers of BzCH(CN)2 and BzCH(CN)CO2Et with NH2OH yielded 5-aminoisoxazoles carrying a CN or CO2Et group, resp., in o-position to the amino group. NH2OH.HCl (1.6 g.) in 8.3 cc. 10% aqueous NaOH treated at 25° with 4.2 g. Ph(MeO)C:C(CN)2 (I) in small portions, stirred 3 hrs., filtered, and the residue dissolved in warm MeoH and reprecipitated with H2O gave 0.4 g. 5-amino-3-phenyl-4-cyanoisoxazole (II), prisms, m. 193°. NH2OH.HCl (0.56 g.) in 3.2 cc. 10% aqueous NaOH treated with stirring with 1.75 g. p-Cl derivative of I in small portions below 30°, stirred 3 hrs. and filtered, and the residue reprecipitated from MeOH with H2O gave 1.25 g. p-Cl derivative of II, m. 205°. NH2OH.HCl (0.35 g.) in 2 cc. 10% aqueous NaOH treated with stirring with 1 g. Ph(MeO)C:C(CN)2 (III) in small portions below 25°, stirred 3 hrs., and filtered gave 0.95 g. 4-CO2Et analog (IV) of I, m. 123°(MeOH). NH2OH.HCl (0.3 g.) in 2 cc. 10% aqueous NaOH treated with stirring with 1.5 g. p-NO2 derivative of III in small portions below 30°, stirred 3 hrs., and filtered yielded 1.2 g. p-NO2 derivative of IV, m. 208°(MeOH). IV (2.2 g.) added to 0.5 g. Na in 20 cc. EtOH, refluxed 3 hrs., evaporated, and the residue dissolved in H2O, acidified with dilute HCl, and filtered gave 1.55 g. 3-phenyl-4-cyano-5-isoxazolone (V), m. 195° (3:1 H2O-HCl). V (0.9 g.) in 20 cc. dry Et2O treated dropwise with cooling with CH2N2-Et2O, after the N evolution ceased treated with a small excess of CH2N2, evaporated, and the residue dried on a clay plate gave 0.7 g. 5-methoxy-3-phenyl-4-cyanoisoxazole (VI), m. 100° (50% aqueous MeOH). VI (0.5 g.) treated with 2.5 cc. piperidine and 2.5 cc. H2O, heated to solution, diluted with iced H2O, and filtered yielded 0.35 g. 5-piperidino analog of II, m. 84° (MeOH). VI (1 g.) and 0.5 g. H2NC(:NH)NH2.HCl added to 0.15 g. Na in 20 cc. absolute EtOH, refluxed 3 hrs., cooled, and filtered gave 0.75 g. 4,6-diamino-3-phenylisoxazolo[5,4-d]pyrimidine, m. 256° (glacial AcOH). In addition to this study using Ethyl 5-amino-3-phenylisoxazole-4-carboxylate, there are many other studies that have used Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9SDS of cas: 29278-09-9) was used in this study.

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).SDS of cas: 29278-09-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Reference of Ethyl 5-amino-3-phenylisoxazole-4-carboxylateOn September 30, 1986 ,《Heterocyclic β-enaminoesters. 45. Complexes of 5-[(triphenylphosphoranylidene)amino]-1,2- and -1,3-oxazole-4-carboxylate esters with metals of the second subgroup》 was published in Chemiker-Zeitung. The article was written by Wamhoff, Heinrich; Horlemann, Norbert; Zhu, Naijue; Guo, Fang. The article contains the following contents:

MLCl2 [L = Et 5-(triphenylphosphoranylideneamino)-3-phenyl-1,2-oxazole-4-carboxylate (L’), M = Zn, Hg; L = Et 5-(triphenylphosphoranylideneamino)-2-phenyl-1,3-oxazole-4-carboxylate, M = Zn, Cd, Mg] and L were prepared and characterized by elemental anal., spectral (IR, 1H and 13C NMR) and x-ray crystallog. methods. Crystals of ZnLCl2 (L = L’) are monoclinic, space group P21, with a 1131.7(2), b 1118.7(27), c 1246.8(2) Å, β 114.25(1)°, d.(x-ray) = 1.45 g cm-3, Z = 2, and R = 0.079 for 1409 reflections with I > 2.5σ. L’ coordinates via imino N and ester carbonyl O atoms. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9Reference of Ethyl 5-amino-3-phenylisoxazole-4-carboxylate)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Reference of Ethyl 5-amino-3-phenylisoxazole-4-carboxylate

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

The author of 《The fulminic synthesis of isoxazoles. V. Nitrile oxides》 were Quilico, A.; Speroni, G.. And the article was published in Gazzetta Chimica Italiana in 1946. Application of 29278-09-9 The author mentioned the following in the article:

cf. C.A. 39, 2753.4. With a view to obtaining exptl. facts in support of the hypothesis that the synthesis of isoxazoles from hydroxamic chlorides and β-ketones (cf. Q. and Fusco, C.A. 32, 2117.4) and from arylacetylenes (cf. Weygand, Bauer, and Heynemann, C.A. 22, 1159) involves the addition of the corresponding nitrile oxides to the enolic -CH:C(OH)- group or to the acetylenic triple bond, an investigation was made of the action of benzonitrile oxide (I) on numerous β-ketones, NCCH2CO2Et (II), and various derivatives of C2H2. I does not react with these in neutral or acid medium, but in alk. medium the reaction is both energetic and exothermic. The results show also the parallelism in the behavior of nitrile oxides, aliphatic diazo compounds, and diazoimides in these reactions. The method of Wieland (C.A. 1, 1981) for the preparation of I was modified and better operating conditions established. Cold 14% aqueous NaOH (25 cc.) was added slowly to a suspension of 5 g. PhC(:NOH)Cl in 50 cc. ice-water, and the mixture was agitated several min. until the product solidified, filtered through a porous plate (kept cold with CO2 snow), and dried at a very low temperature The yield was 3.5 g. (90%), and the product should be used immediately. Alc. I (2 g. in 10 cc.) and 2.2 g. AcCH2CO2Et, treated with several drops of 20% aqueous NaOH (exothermic), allowed to stand 2 days, the precipitate separated, the mother liquor concentrated, the combined yields (77%) saponified by heating with a slight excess of 50% aqueous NaOH, the EtOH evaporated, diluted with water, filtered, acidified with dilute H2SO4, and the precipitate purified by EtOH, yielded O.N:CPh.C(CO2H):CMe, m. 189-90° (cf. Q. and Fusco, C.A. 32, 2117.4). By the same procedure I and BzCH2CO2Et yielded O.N:CPh.C(CO2H): CPh, m. 233° (cf. Fusco, C.A. 33, 8611.4). The yield was not given, but 3.1 g. of the Et ester was obtained as intermediate product. Likewise, 3.15 g. EtO2CCOCH2CO2Et and 2 g. I gave, after purification by C6H6, 0.5 g. O.N:CPh.C(CO2H):CCO2H, m. 86° (cf. Q. and Fusco, loc. cit.) Alc. I (2 g.) and 1.9 g. II, made alk. with NaOH (heat was evolved and the mixture turned greenish yellow) and concentrated, yielded 1.6 g. O.N:CPh.C(CO2Et):CNH2 (III), m. 122-3°, which, treated with excess hot aqueous NaOH and allowed to stand overnight, precipitated O.N:CPh.CH:CNH2, m. 109-10°. III (0.5 g.), dissolved in boiling aqueous Ba(OH)2, cooled, acidified with AcOH, and the precipitate purified by EtOH, gave O.N:CPh.C(CO2H):CNH2, m. 179-80° (cf. Fusco, loc. cit.). Alc. I (2 g. in 25 cc.), 1.7 g. Ac2CH2, and 5-6 drops 20% NaOH (evolved heat and turned dark yellow), allowed to stand 24 hrs., evaporated, and the product purified by EtOH, gave 2.4 g. O.N:CPh.CAc:CMe, m. 60° (cf. Fusco, loc. cit.). Prepared similarly from I and BzCH2Ac, O.N:CPh.CBz:CMe m. 115-16° (cf. Fusco, loc. cit.). Alc. I (2 g. in 25 cc.), 1.7 g. PhCCH, and 4-5 drops 20% NaOH (much heat evolved; had to be cooled with ice to avoid violent boiling), allowed to stand and the precipitate purified from hot EtOH, gave 2.7 g. O.N:CPh.CH:CPh, m. 141° (cf. Goldschmidt, Ber. 28, 2540(1895)). The solution of alc. HCCCO2H (1.5 g. in 10 cc.), alc. I (2 g. in 10 cc.), and several drops 20% NaOH (heat evolved; turned yellow), when evaporated, the residue allowed to crystallize (several days), dissolved in EtOH, filtered, the filtrate evaporated, and the residue purified by hot ligroin, gave O.N:CPh.CH:CCO2H, m. 176-8° (cf. Betti, Gazz. chim. ital. 45, I, 362(1915)). Alc. MeCCCO2H (cf. Feist, Ann. 345, 104(1906)) (1.4 g. in 10 cc.), 2 g. I, and 4-5 drops 20% NaOH, allowed to stand 2 days, concentrated, the crystallized mass dissolved in hot aqueous Na2CO3 (dark yellow solution), acidified, and the precipitate purified by EtOH, gave a small yield of O.N:CPh.C(CO2H):CMe (IV), m. 187-8° (cf. Betti, loc. cit.). Treated with SOCl2 on a steam bath, the excess SOCl2 evaporated in vacuo, PhNH2 in Et2O added, and the product purified by EtOH, IV formed an anilide, m. 192-3°. Alc. PhCCCO2H (2.4 g. in 20 cc.), alc. I (2 g.), and several drops 20% NaOH (heat evolved) when allowed to stand, filtered, the mother liquor concentrated, and the combined products purified by EtOH, gave 3.1 g. O.N:CPh.C(CO2H):CPh, m. 233° (decomposition) (cf. Betti, loc. cit; B. and Berlingozzi, Gazz. chim. ital. 45, II, 156(1915) and C.A. 16,932; Q. and Fusco, loc. cit.). Alc. HO2CCCCO2H (2 g. in 10 cc.), 2 g. I, and several drops 20% NaOH, when evaporated to a pitchy mass which was taken up in boiling water, filtered, the yellow filtrate concentrated to a small volume, concentrated HCl added, the mixture allowed to stand, and the slowly separating product pressed and dried in an oven at 100°, gave a very small yield of a compound which, although in too small quantity to analyze, was probably O.N:CPh.C(CO2H):CCO2H, m. approx. 150° (decomposition). Under the same conditions, I did not react with PhCCPh, MeCCPh, and PhCCCCH. It remains to be explained how in the case of acetylenic carboxylic acids like MeCCCO2H and PhCCCO2H, the addition of a quantity of alkali much less than that necessary to neutralize the acid was capable of starting the reaction with I and giving good yields. The velocity of the transformation of I into a form capable of reacting with the HCCH derivative must be greater than the velocity of salification in alc. medium. In the experiment, the researchers used Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9Application of 29278-09-9)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Reduction of nitro compounds, RNO2, by hydrogen or other reducing agents produces primary amines cleanly (i.e., without a mixture of products), but the method is mostly used for aromatic amines because of the limited availability of aliphatic nitro compounds. Reduction of nitriles and oximes (R2C=NOH) also yields primary amines.Application of 29278-09-9

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

In 1988,Tetrahedron Letters included an article by Lipshutz, Bruce H.; Reuter, Deborah C.. COA of Formula: C12H12N2O3. The article was titled 《Cyclopeptide alkaloid model studies. A two-step conversion of 5-aminoisoxazoles to amino acid bis-amides》. The information in the text is summarized as follows:

Thermolyses of substituted 5-aminoisoxazoles I (R = CH2SPh, CH2OCH2Ph, CH2OMe, Me, H, Ph, CH2 Ph, Pr), readily available from common starting materials, lead to azirines II in good yields. Subsequent hydration affords bisamide derivatives of amino acids, e.g. B2NHCHRCON(CH2Ph)2.Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9COA of Formula: C12H12N2O3) was used in this study.

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.COA of Formula: C12H12N2O3

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

In 1983,Gazzetta Chimica Italiana included an article by Ponticelli, Fabio; Tedeschi, Piero. Synthetic Route of C12H12N2O3. The article was titled 《Ethyl 5-imino-2-methyl-2,5-dihydroisoxazole-3- and 4-carboxylates: synthesis and alkaline ring opening》. The information in the text is summarized as follows:

Methylation of I (R = Me, Ph, R1 = CO2Et, R2 = H, Me; R = CO2Et, R1 = Me, Ph, R2 = H; R = Me, Ph, R1 = CO2H, R2 = H) by FSO3Me gave II which (R = Me, Ph, R1 = CO2Et, R2 = H) were heated with alc. NaOH to give III (R1 = CN) which were hydrolyzed to give IV (R3 = Me, Ph). Treatment of the latter with SOCl2 gave MeN(OH)C(:NH)CH2CO2Et.HCl; catalytic hydrogenation gave MeNHC(:NH)CH2COR3.HCl. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9Synthetic Route of C12H12N2O3)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Synthetic Route of C12H12N2O3

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

《Discovery of a Potent and Selective NF-κB-Inducing Kinase (NIK) Inhibitor That Has Anti-inflammatory Effects in Vitro and in Vivo》 was written by Li, Zhiqiang; Li, Xinzhi; Su, Ming-Bo; Gao, Li-Xin; Zhou, Yu-Bo; Yuan, Bingchuan; Lyu, Xilin; Yan, Ziqin; Hu, Chujiao; Zhang, Hao; Luo, Cheng; Chen, Zheng; Li, Jia; Zhao, Yujun. Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol And the article was included in Journal of Medicinal Chemistry on April 23 ,2020. The article conveys some information:

The overexpression of NIK plays a critical role in liver inflammatory diseases. Treatment of such diseases with small-mol. NIK inhibitors is a reasonable but underexplored approach. In this paper, we reported the discovery of a potent and selective NIK inhibitor I (XT2). The compound I inhibited the NIK kinase with an IC50 value of 9.1 nM in vitro, and it also potently suppressed NIK activities in intact cells. In isogenic primary hepatocytes, treatment with I efficiently suppressed the expressions of NIK-induced genes. The compound I was orally bioavailable in mice with moderate systemic exposure. In a NIK-associated mouse liver inflammation model, the compound I suppressed CCl4-induced upregulation of ALT, a key biomarker of acute liver injury, and also decreased immune cell infiltration into the injured liver tissue. Overall, these studies provide examples that an NIK inhibitor is able to suppress toxin-induced liver inflammations, which indicates its therapeutic potentials for the treatment of liver inflammatory diseases. In addition to this study using 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol, there are many other studies that have used 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol(cas: 1202769-66-1Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol) was used in this study.

2-(5-Methylisoxazol-3-yl)but-3-yn-2-ol(cas: 1202769-66-1) belongs to isoxazoles. Isoxazoles is an oxygen-containing azole derivative found in some natural products such as amantine, as well as in several drugs, including COX-2 inhibitors and furoxan oxide (a nitric oxide donor). body). Safety of 2-(5-Methylisoxazol-3-yl)but-3-yn-2-olIsoxazoles 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.

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem

Beccalli, Egle M.; Manfredi, Amadea; Marchesini, Alessandro published an article in Journal of Organic Chemistry. The title of the article was 《Alkynes from 5-aminoisoxazoles》.Formula: C12H12N2O3 The author mentioned the following in the article:

Diazotization of 5-aminoisoxazoles I [R = Ph, H, CO2Et, Me; R1 = CONH2, CO2Et, p-O2NC6H4, 4-pyridyl, etc. (≥1 of R and R1 is an electron-withdrawing group)] by reaction with NaNO2 in AcOH-H2O afforded the corresponding RCCR1. A reaction path involving an intermediate isoxazol-5-yl radical is proposed. In the part of experimental materials, we found many familiar compounds, such as Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9Formula: C12H12N2O3)

Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Formula: C12H12N2O3

Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem