Day: April 6, 2022

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Catalyst-controlled regioselective nitrosocarbonyl aldol reaction of deconjugated butenolides, published in 2020-02-21, which mentions a compound: 591-12-8, mainly applied to heterofunctionalized butenolide regioselective preparation; deconjugated butenolide nitrosocarbonyl aldol, Related Products of 591-12-8.

An unprecedented regiodivergent nitrosocarbonyl aldol reaction of γ-substituted deconjugated butenolides was described. While Lewis base catalyst quinidine leveraged O-selective nitrosocarbonyl aldol reaction exclusively at the γ-position of deconjugated butenolides to produce γ-substituted-butenolides I [R = Me, n-Pr, PhCH2, etc.; R1 = t-BuO, OCH2CH=CH2, PhCH2O, 4-MeC6H4, etc.], Lewis acid catalyst Cu(OTf)2 steered the competitive N-selective nitrosocarbonyl aldol reaction at the β-position, resulting in hetero-β,γ-difunctionalized-butenolides II [R2 = Me, Ph, 4-MeC6H4CH2, PhCH2; R3 = t-Bu, PhCH2, 1-naphthyl, etc.]. Both processes were amenable to a broad range of substrates and scalable, while the latter one represented a rare example of one-pot hetero-β,γ-difunctionalization of butenolide scaffolds.

There is still a lot of research devoted to this compound(SMILES：O=C1OC(C)=CC1)Related Products of 591-12-8, and with the development of science, more effects of this compound(591-12-8) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Piperidin-4-amine dihydrochloride(SMILESS: NC1CCNCC1.[H]Cl.[H]Cl,cas:35621-01-3) is researched.Category: benzofurans. The article 《Polyamine Analog Regulation of NMDA MK-801 Binding: A Structure-Activity Study》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:35621-01-3).

A series of analogs and homologs of spermine were synthesized, and their impact on MK-801 binding to the N-methyl-D-aspartate (NMDA) receptor was evaluated. These tetraamines encompass both linear and cyclic compounds The linear mols. include norspermine, N1,N11-diethylnorspermine, N1,N12-bis(2,2,2-trifluoroethyl)spermine, homospermine, and N1,N14-diethylhomospermine. The cyclic tetraamines consist of the piperidine analogs N1,N3-bis(4-piperidinyl)-1,3-diaminopropane, N1,N4-bis(4-piperidinyl)-1,4-diaminobutane, N1,N4-bis(4-piperidinylmethyl)-1,4-diaminobutane, and N1,N4-bis[2-(4-piperidinyl)ethyl]-1,4-diaminobutane and the pyridine analogs N1,N3-bis(4-pyridyl)-1,3-diaminopropane, N1,N4-bis(4-pyridyl)-1,4-diaminobutane, N1,N4-bis(4-pyridylmethyl)-1,4-diaminobutane, and N1,N4-bis[2-(4-pyridyl)ethyl]-1,4-diaminobutane. This structure-activity set makes it possible to establish the importance of charge, intercharge distance, and terminal nitrogen substitution on polyamine-regulated MK-801 binding in the NMDA channel. Four families of tetraamines are included in this set: norspermines, spermines, homospermines, and tetraazaoctadecanes. Calculations employing a SYBYL modeling program revealed that the distance between terminal nitrogens ranges between 12.62 and 19.61 Å. The tetraamines are constructed such that within families cyclics and acyclics have similar lengths but different nitrogen pKa’s and thus different protonation, or charge, states at physiol. pH. The pKa values for all nitrogens of each mol. and its protonation state at physiol. pH are described. The modifications at the terminal nitrogens include introduction of Et and β,β,β-trifluoroethyl groups and incorporation into piperidinyl or pyridyl systems. The studies clearly indicate that polyamine length, charge, and terminal nitrogen substitution have a significant effect on how the tetraamine regulates MK-801 binding to the NMDA receptor. Thus a structure-activity basis set on which future design of MK-801 agonists and antagonists can be based is now available.

There is still a lot of research devoted to this compound(SMILES：NC1CCNCC1.[H]Cl.[H]Cl)Computed Properties of C5H14Cl2N2, and with the development of science, more effects of this compound(35621-01-3) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of 3-pyridinols. III. Synthesis of pyridoxine skeletons from 4-methyloxazole》. Authors are Yoshikawa, Toru; Ishikawa, Fumiyoshi; Naito, Takeo.The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Recommanded Product: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride. Through the article, more information about this compound (cas:148-51-6) is conveyed.

Pyridoxine dimethyl ether (I) and 4-deoxypyridoxine (II) were synthesized from 4-methyloxazole (III). 3-Cyano-5-hydroxy-6-methylpyridine (IV) was converted via the 4-CN derivative (V) to pyridoxine by the method of Okamoto and Tani (CA 54, 22644d). (MeOCH2CHBr)2 (5.5 g.) refluxed 1 hr. with 1.23 g. KOH in 12 cc. MeOH gave 2.2 g. MeOCH2CBr:CHCH2OMe (VI), b12 75-8°. VI (5.5 g.) and 3.5 g. CuCN heated 7 hrs. at 150° in an autoclave yielded 2.9 g. MeOCH2CH:C(CN)CH2OMe (VII), b8 84-6°. III (0.8 g.), 2.1 g. VII, 0.2 cc. H2O, and 4 cc. AcOH heated 40 hrs. at 95°, and the crude product chromatographed on Al2O3 yielded 2-methyl-4,5-bis(methoxymethyl)-3-pyridinol-HCl (VIII.HCl), m. 143-4° (iso-PrOH); picrate m. 168°. III (0.80 g.), 2.3 g. MeCH:CHCO2Et, 0.18 cc. H2O, and 3 cc. AcOH heated 20 hrs. at 90° in a sealed tube gave 0.2 g. (crude) Et 5-hydroxy-4,6-dimethylnicotinate, m. 146-8° (Me2CO). VIII (80 mg.) in 15 cc. dry tetrahydrofuran treated 72 hrs. at room temperature with 50 mg. LiAlH4 in 15 cc. dry tetrahydrofuran, and the filtered mixture acidified to pH 2 with dilute HCl and evaporated gave II.HCl, m. 255-7° (decomposition) (EtOH). IV (4.0 g.) in 90 cc. AcOH heated 1 hr. at 100° with 6 cc. 30% H2O2, treated twice with addnl. 6 cc. 30% H2O2 each time 1 and 4 hrs. gave 3.3 g. 5hydroxy-6-methylnicotinonitrile 1-oxide (IX), m. 278-80° (decomposition). IX (0.7 g.) and 0.7 g. Et2SO4 heated 2 hrs. at 100-10° gave 0.31 g. 1-ethoxy-2-methyl-3-hydroxy-5-cyanopyridinium ethosulfate, m. 129-30°. IX (0.6 g.) and 0.55 g. Me2SO4 heated 2 hrs. at 100-10°, and the resulting sirup added in 5 cc. H2O dropwise with shaking at 5-7° to 0.65 g. KCN in 8 cc. H2O and kept 1.5 hr. at room temperature gave 0.55 g. V, m. 189-90°.

There is still a lot of research devoted to this compound(SMILES：OC1=C(C)C(CO)=CN=C1C.[H]Cl)Recommanded Product: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride, and with the development of science, more effects of this compound(148-51-6) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthetic and natural phellandrene.》. Authors are Kondakow, J.; Schindelmeiser, J..The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Related Products of 148-51-6. Through the article, more information about this compound (cas:148-51-6) is conveyed.

[Machine Translation of Descriptors]. Carvomenthene, from carvomenthylchloride represented, became after REYCHLER into tertiary carvomenthol and over with 12 mm and 83.5-84.5° boiling. Chloride, D204; 0.932, into tertiary carvomenthene, C10H18, transferred. Boiling point 174-176°; D204; 0.811; nD = 1.45709, molecular refraction 46.23. Dibromide, under strong cooling in petroleum-ether prepared, Kp11; 130-144°. D204; 1.208, optical-inactively, separates no HBr, however alcoholic KOH supplies a hydrocarbon, from the main quantity with 175-180° with boiling D204; 0.825, nD = 1.46693, the smaller part with 180-185°. D204; 0.828, nD = 1.4673; molecular refraction 45.56. Both optical-inactive fractions color intensively raspberry red in a solution of acetic anhydride by H2SO4 and are undoubtedly different from the output hydrocarbon. Under consideration of the formation of the new hydrocarbon from carvomenthol author writes it from SEMMLER, (Ber. German Chem. Society 36. 1779; C. 1903. II. 116) for the phellandrene determined constitution without being able to prove the identity. Phellandrene from phellandrum aquaticum, boiling point 165-168°, D204; 0.844, nD = 1.47575, [α] D20 = 8° 37′. Molecular refraction a mixture of monochloride and dichloride gives 45.28, which probably contains an optical-inactive isomer, with HCl in glacial acetic acid. Monochloride, C10H17Cl, Kp11; 86°, melting point about 110° in the melted out tube, optically dextrorotatory. Dichloride, C10H18Cl2, Kp16; 122.5-125°, D204, 1.006, nD20 = 1.48516.

There is still a lot of research devoted to this compound(SMILES：OC1=C(C)C(CO)=CN=C1C.[H]Cl)Related Products of 148-51-6, and with the development of science, more effects of this compound(148-51-6) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Bromo-3-methoxypropanoic acid( cas:65090-78-0 ) is researched.Electric Literature of C4H7BrO3.Jin, Shu-yun; Yu, Di-hu; Li, Yong published the article 《Study on by-products in N-benzyl-2-bromo-3-methoxypropionamide by mixed anhydride methods》 about this compound( cas:65090-78-0 ) in Huaxue Shijie. Keywords: byproduct benzyl bromo methoxypropionamide mixed anhydride. Let’s learn more about this compound (cas:65090-78-0).

N-Benzyl-2-bromo-3-methoxypropionamide was synthesized from 2-bromo-3-methoxypropionic acid by mixed anhydride methods. The main impurities were separated and analyzed. Furthermore, the mechanism of the production of the main impurities was discussed. The mol. structures of impurities were confirmed by 1 H NMR, 13C NMR, IR.

There is still a lot of research devoted to this compound(SMILES：O=C(O)C(Br)COC)Electric Literature of C4H7BrO3, and with the development of science, more effects of this compound(65090-78-0) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Preparation of 3-hydroxy-5-hydroxymethyl-2,4-dimethylpyridine (4-deoxyadermine)》. Authors are Wibaut, J. P.; Uhlenbroek, J. H.; Kooijman, E. C.; Kettenes, D. K..The article about the compound:5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloridecas:148-51-6,SMILESS:OC1=C(C)C(CO)=CN=C1C.[H]Cl).Synthetic Route of C8H12ClNO2. Through the article, more information about this compound (cas:148-51-6) is conveyed.

The preparation of 4-deoxyadermine (I) as described earlier (CA 38, 32849) was improved to give a total yield 15%. Ac2CH2 (25 g.) was slowly added to a refluxing solution of 21 g. NCCH2CONH2 in 150 ml. EtOH and 3 ml. piperidine to give 97% 2-hydroxy-3-cyano-4,6-dimethylpyridine (II), m. 294°, which on nitration with HNO3 (d. 1.52) in Ac2O at 45-50° gave a 5-nitro derivative (III) m. 268° in 70% yield. A mixture of 50 g. dry III and 65 g. PCl5 was treated with 30 ml. POCl3 and heated to 130°, to yield 71% 2,4-dimethyl-3-nitro-5-cyano-6-chloropyridine, m. 112-13° (EtOH), which was reduced by Pd-C in MeOH and aqueous HCl to give 70-5% 2,4-dimethyl-3-amino 5-aminomethylpyridine di-HCl salt monohydrate (IV), m. 310° (decomposition). The reaction of IV with Ba(NO2)2 and H2SO4 at 0°, and subsequent heating to 90° afforded 45% I, m. 264°.

There is still a lot of research devoted to this compound(SMILES：OC1=C(C)C(CO)=CN=C1C.[H]Cl)Synthetic Route of C8H12ClNO2, and with the development of science, more effects of this compound(148-51-6) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《β-Amino acids. IV. β-Methionine and β-ethionine》. Authors are Birkofer, Leonhard; Storch, Ingeborg.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).Formula: C4H7BrO3. Through the article, more information about this compound (cas:65090-78-0) is conveyed.

cf. C.A. 49, 2317d. HO2CCHAcCH2CO2Et and NaH gave the Na salt, which with ClCH2SMe yielded EtO2CAc(CH2SMe)CH2CO2Et (I), b3 153° (2,4-dinitrophenylhydrazone, m. 92-3°). Refluxed 10 hrs. with 18% HCl I gave AcCH(CH2SMe)CH2CO2H, isolated as the Et ester (II), b3 123° (2,4-dinitrophenylhydrazone, m. 62-3°), as well as AcC(:CH2)CH2CO2H (2,4-dinitrophenylhydrazone, m. 210°), and 3-acetyl-γ-butyrolactone (2,4-dinitrophenylhydrazone, m. 193°). I refluxed with HCl only 4 hrs. gave mono-Et 2-acetyl-2-(methylthiomethyl)succinate, b0.001 115-17° (2,4-dinitrophenylhydrazone, m. 169-70°). I was saponified with Ba(OH)2 to HO2CCH(CH2SMe)CH2CO2H, m. 114-15°. II and HN3 in the presence of HCl gave β-methionine (III), m. 197-8° (picrolonate, m. 190-2°; 3,5-dinitrobenzoyl derivative, m. 200°). MeSCH2CH:CHCO2H, m. 58.5°, obtained from MeSCH2CHO and CH2(CO2H)2 (IV), gave III with NH3 in a sealed tube at 150-60°. EtSNa, obtained from EtSH with Na, and bromoacetal gave EtSCH2CH(OEt)2, converted by HCl to the aldehyde, b14 45-6°, which with IV gave EtSCH2CH:CHCO2H, which with NH3 in a sealed tube yielded β-ethionine (V), m. 198° (picrolonate, m. 180-3°). III and V do not react with aqueous ninhydrin, but give a blue color with it in 95% BuOH-5% 2N HOAc.

There is still a lot of research devoted to this compound(SMILES：O=C(O)C(Br)COC)Formula: C4H7BrO3, and with the development of science, more effects of this compound(65090-78-0) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Piperidin-4-amine dihydrochloride, is researched, Molecular C5H14Cl2N2, CAS is 35621-01-3, about Palladium-mediated N-arylation of heterocyclic diamines: insights into the origin of an unusual chemoselectivity.Recommanded Product: 35621-01-3.

The chemoselectivity of the palladium-mediated reaction of bromobenzene with various heterocyclic diamines was studied. Whatever the ligand used, 3-aminopyrrolidine underwent arylation of the secondary amine function (>82%), whereas the more flexible 3-aminoazepine was arylated on its primary function (>70%). The ratio “”arylation of primary amine vs. arylation of secondary amine”” of 3-aminopiperidine with bromobenzene varied from 90:10 (BINAP, electron-enriched and hindered biphenyls L2 or L3) to 32:68 with the Josiphos-type ligand L10. The same trend was observed when 4-aminopiperidine was used (82:18 with L2 and 17:83 with L10). This selectivity can be tuned by the choice of aryl halide partners having different steric and electronic properties. A cooperative effect of both nitrogens of diamines during the reaction was deduced from competitive experiments Finally, 13C and 31P NMR experiments, carried out with 3-aminopyrrolidine at room temperature, support a fast coordination of the primary amine to the metal. Indeed, a palladium complex resulting from the unusual displacement of one phosphine group of the intermediate ArPdX(BINAP) by the primary amino group was characterized.

There is still a lot of research devoted to this compound(SMILES：NC1CCNCC1.[H]Cl.[H]Cl)Recommanded Product: 35621-01-3, and with the development of science, more effects of this compound(35621-01-3) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 18436-73-2, is researched, Molecular C10H8ClN, about Potent antiviral activity of novel multi-substituted 4-anilinoquin(az)olines, the main research direction is anilinoquinazoline anilinoquinoline preparation antiviral agent Dengue virus; 4-Anilinoquinazoline; 4-Anilinoquinoline; Antiviral; Dengue Virus; Flavivirus.Recommanded Product: 18436-73-2.

Screening a series of 4-anilinoquinolines and 4-anilinoquinazolines enabled identification of potent novel inhibitors of dengue virus (DENV). Preparation of focused 4-anilinoquinoline/quinazoline scaffold arrays led to the identification of a series of high potency 6-substituted bromine and iodine derivatives The most potent compound 6-iodo-4-((3,4,5-trimethoxyphenyl)amino)quinoline-3-carbonitrile inhibited DENV infection with an EC50 = 79 nM. Crucially, these compounds showed very limited toxicity with CC50 values >10μM in almost all cases. This new promising series provides an anchor point for further development to optimize compound properties.

There is still a lot of research devoted to this compound(SMILES：CC1=C2N=CC=C(Cl)C2=CC=C1)Recommanded Product: 18436-73-2, and with the development of science, more effects of this compound(18436-73-2) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-(hydroxymethyl)-2,4-dimethylpyridin-3-ol hydrochloride( cas:148-51-6 ) is researched.Category: pyrimidines.Chaudhary, Chhabi Lal; Chaudhary, Prakash; Dahal, Sadan; Bae, Dawon; Nam, Tae-gyu; Kim, Jung-Ae; Jeong, Byeong-Seon published the article 《Inhibition of colitis by ring-modified analogues of 6-acetamido-2,4,5-trimethylpyridin-3-ol》 about this compound( cas:148-51-6 ) in Bioorganic Chemistry. Keywords: aminopyridinol analog preparation inflammatory bowel disease SAR; 6-Aminopyridin-3-ol; Adhesion; Angiogenesis; Inflammatory bowel disease; Ring modification; Structure-activity relationship; TNF-α. Let’s learn more about this compound (cas:148-51-6).

6-Aminopyridin-3-ol scaffold has shown an excellent anti-inflammatory bowel disease activity. Various analogs with the scaffold were synthesized in pursuit of the diversity of side chains tethering on the C(6)-position. SAR among the analogs was investigated to understand the effects of the side chains and their linkers on their anti-inflammatory activities. In this study, structural modification moved beyond side chains on the C(6)-position and reached to pyridine ring itself. It expedited to synthesize diverse ring-modified analogs of a representative pyridine-3-ol, 6-acetamido-2,4,5-trimethylpyridin-3-ol. In the evaluation of compounds on their inhibitory actions against TNF-α-induced adhesion of monocytic cells to colonic epithelial cells, an in vitro model mimicking colon inflammation, the effects of compounds I , II, and III were greater than tofacitinib, an orally available anti-colitis drug, and compound dehydroxylated analog II exhibit the greatest activity. In addition, TNF-α-induced angiogenesis, which permits more inflammatory cell migration into inflamed tissues, was significantly blocked by compounds I and II in a concentration-dependent manner. In the comparison of in vivo therapeutic effects of compounds I , II, and III on dextran sulfate sodium (DSS)-induced colitis in mice, compound dehydroxylated analog II was the most potent and efficacious, and compound demethylated analog III was better than compound I which exhibited a similar degree of inhibitory effect to tofacitinib.

There is still a lot of research devoted to this compound(SMILES：OC1=C(C)C(CO)=CN=C1C.[H]Cl)Category: pyrimidines, and with the development of science, more effects of this compound(148-51-6) can be discovered.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia