Month: April 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》. Authors are Baumgarten, Henry E.; Pedersen, Donald L.; Hunt, Mack W..The article about the compound:2-Amino-5-chlorobenzaldehydecas:20028-53-9,SMILESS:NC1=CC=C(Cl)C=C1C=O).Reference of 2-Amino-5-chlorobenzaldehyde. Through the article, more information about this compound (cas:20028-53-9) is conveyed.

cf. C.A. 50, 8672d. Crude, moist 4,2-Cl(H2N)C6H3CHO (7 g.), 2.9 g. NaNO2, and 75 g. crushed ice slurried in a Waring blender, treated with 9 cc. concentrated HCl and 50 g. crushed ice in 1 portion, blended 5 min. while adding periodically crushed ice, 4.3 cc. MeNO2 in 5 cc. EtOH added slowly with stirring to 5.7 g. KOH in 3.5 l. iced H2O, the solution treated with 3.3 g. NaOAc, the diazonium salt solution added slowly, the mixture allowed to stand 20 min. and filtered, the residue blended about 5-10 min. with 1.3 g. KOH in 50 cc. H2O, the mixture poured into a beaker, allowed to stand 2.5 hrs., and filtered, and the residue dried overnight (1.51 g.) and recrystallized from Me2CO or EtOAc yielded 1.1 g. 7-chloro-3-nitrocinnoline (I), yellow needles, m. 165.6-66° (all m.ps. are corrected). A similar run with a 4-fold larger amount of each reagent was carried out, the resulting yellow solid blended about 10 min. with 5.2 g. KOH in 200 cc. H2O, kept 2.5 hrs., and filtered, the brown residue refluxed 2 hrs. with 300 cc. Me2CO and filtered, and the filtrate treated with C, concentrated to about 75 cc., and cooled, giving 5.5-14.0 g. 5,2-Cl(AcCH:CH)C6H3NHN:CHNO2, yellow-orange needles, m. 234-5° (Me2CO). 5,2-Cl(O2N)C6H3CHO (15.6 g.) in 360 cc. hot EtOH added to 180 g. FeSO4.7H2O in 600 cc. H2O at 90°, the mixture treated slowly during 10 min. with 600 cc. concentrated NH4OH and steam-distilled, the 1st 300-500 cc. distillate discarded, and the following 2 l. distillate cooled to 5°, saturated with NaCl, and filtered yielded 6.5-7.0 g. crude 5,2-Cl(H2N)C6H3CHO (II), m. 73.5-4.5°. Crude moist II (7.0 g.) was converted as described for the preparation of I to 5.1 g. (crude) 6-Cl isomer of I, yellow plates, m. 227-8° (EtOAc). 6-Aminopiperonal (9.0 g.) was converted in the usual manner to nitroformaldehyde 4,5-methylenedioxy-2-formylphenylhydrazone and this to 1.96 g. (crude) 6,7-methylenedioxy-3-nitrocinnoline, cream-colored needles, m. 255-310° (indefinite). 3-Nitrocinnoline (13.8 g.) in 110 cc. AcOH and 55 cc. H2O treated during about 5 min. with 11 g. Fe powder, refluxed 1 hr., poured into 300 g. cold 33% aqueous KOH, kept overnight, and filtered through Celite, the filter cake washed with H2O, suspended in 150 cc. absolute EtOH, heated to boiling, filtered, and again extracted with 150 cc. and 100 cc. absolute EtOH, the combined filtrates evaporated, and the residue recrystallized from 250 cc. C6H6 gave 8.0 g. 3-aminocinnoline (III), m. 165-6°; 2nd crop, 1.1 g. I (3.0 g.) reduced similarly gave 2.2 g. 7-Cl derivative of III, bright yellow plates, m. 202° (decomposition). II (3.0 g.) gave similarly 1.91 g. 6-Cl derivative of III, bright yellow needles, m. 215° (decomposition). ο-O2NC6H4CHO (IV) (10 g.) in 50 cc. absolute MeOH treated with 2 drops concentrated HCl and 0.75 g. CaCl2, the mixture kept 6 days in a desiccator over CaCl2, filtered, neutralized with NaOMe in MeOH, and evaporated, and the oily residue distilled gave 11.4 g. ο-O2NC6H4CH(OMe)2 (V), b27 146-9°, n25D 1.5265. IV (100 g.) in 750 cc. C6H6 and 50 cc. absolute MeOH refluxed 28 hrs. with 2 g. p-MeC6H4SO3H with the azeotropic removal of H2O, concentrated by removing 500 cc. distillate, neutralized with NaOMe, and worked up in the usual manner yielded 116 g. V. IV (15 g.) in 250 cc. C6H6 and 35 cc. absolute MeOH refluxed 35 hrs. with 2 g. Amberlite IR-120 with the azeotropic removal of H2O, filtered, and distilled gave 18.4 g. V. IV (10 g.) in 250 cc. C6H6 and 25 cc. (CH2OH)2 refluxed 30 hrs. with 0.25 g. p-MeC6H4SO3H with the azeotropic removal of H2O, concentrated by removal of about 150 cc. distillate, basified with NaOMe to litmus, and fractionated gave 10.3 g. ethylene acetal (VI) of IV, pale yellow oil, b0.7 120.7°, n20D 1.5487. IV (15 g.) in 250 cc. C6H6 and 10 cc. (CH2OH)2, refluxed 30 hrs. with 2 g. Amberlite IR-120 with the azeotropic removal of H2O, filtered, and distilled gave 18.4 g. VI, b0.7 120°. V (5.0 g.), 100 cc. absolute MeOH, and about 1 g. Raney Ni hydrogenated about 1 hr. at 45 lb., filtered, slurried in a Waring blender with 50 cc. H2O, 3.5 g. NaNO2, and 300 g. crushed ice, treated with 25 cc. 6N HCl, and slurried again 20 min. while adding periodically crushed ice, the mixture added dropwise with stirring during 20 min. to a solution of 3.0 g. MeNO2, 10 cc. EtOH, and 5.7 g. KOH in 400 cc. H2O, and the precipitate recrystallized from 1:3 Me2CO-H2O gave 4.3 g. ο-O2NCH:NNHC6H4CH(OMe)2 (VII), bright orange needles, m. 80-1°. VI (4.3 g.), 50 cc. absolute MeOH, and about 0.5 g. Raney Ni hydrogenated, filtered, diazotized in a blender with 3 g. NaNO2, 100 cc. H2O, 300 g. ice, and 22 cc. 6N HCl, added to a solution of 4 g. MeNO2, 10 cc. EtOH, and 7.5 g. KOH in 400 cc. iced H2O, adjusted with cold 1% HCl to pH 3, stirred 20 min. at 5°, and filtered gave 2.5 g. ethylene acetal (VIII) of ο-O2NCH:NNHC6H4CHO (IX), golden yellow plates, m. 83.6-85° (aqueous Me2CO); the filtrate warmed to room temperature and extracted with Et2O, and the extract evaporated gave 1.8 g. IX, m. 156-8°. VII (0.87 g.) added at 95° to 3 cc. concentrated HCl in 200 cc. H2O in a Waring blender, the solution blended 0.5 hr., cooled to 10°, and extracted with Et2O, and the extract worked up gave 0.66 g. IX, m. 157-8°. VIII (0.65 g.) hydrolyzed similarly with 2 cc. concentrated HCl in 150 cc. hot H2O yielded 0.49 g. IX. IX (2.0 g.) in 300 cc. tetrahydrofuran circulated 18 hrs. at 55° through 6 g. dry Amberlite IRA-400, filtered, and evaporated gave 1.0 g. 3-nitrocinnoline, m. 204-5° (aqueous Me2CO).

The article 《Cinnolines. III. Synthesis of bz-substituted 3-nitro- and 3-aminocinnolines》 also mentions many details about this compound(20028-53-9)Reference of 2-Amino-5-chlorobenzaldehyde, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines》. Authors are Lange, Paul P.; Bogdan, Andrew R.; James, Keith.The article about the compound:Methyl 6-bromonicotinatecas:26218-78-0,SMILESS:C1=NC(=CC=C1C(=O)OC)Br).Category: tetrahydrofurans. Through the article, more information about this compound (cas:26218-78-0) is conveyed.

A flow-based synthesis of diversely functionalized indolizines and their aza-analogs is described. These drug-like heterocycles were generated via a tandem Sonogashira/cycloisomerization sequence, starting from widely available 2-bromopyridines and alkynes, employing a simple catalyst system together with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base. E.g., in presence of PdCl2(PPh3)2, CuI, and NEt3, followed by addition of DBU in DMF, Sonogashira/cycloisomerization of Me 6-bromonicotinate and N-methyl-N-propargylbenzylamine gave 71% indolizine derivative (I). The use of flow technol. allows a straightforward and rapid access to a variety of novel compounds, and enables linear scale-up from milligram- to gram-scales without a decrease in yield.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Pang, Lijuan; Bezencon, Jacqueline; Kleeb, Simon; Rabbani, Said; Sigl, Anja; Smiesko, Martin; Sager, Christoph P.; Eris, Deniz; Schwardt, Oliver; Ernst, Beat published the article 《FimH antagonists – solubility vs. permeability》. Keywords: FimH antagonist solubility permeability.They researched the compound: Methyl 6-bromonicotinate( cas:26218-78-0 ).SDS of cas: 26218-78-0. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:26218-78-0) here.

Urinary tract infections (UTIs) caused by uropathogenic Escherichia coli (UPEC) are among the most prevalent infections worldwide. Since frequent antibiotic treatment favors the emergence of antibiotic resistance, efficient non-antibiotic strategies are urgently needed. The first step of the pathogenesis of UTI is the bacterial adherence to urothelial host cells, a process mediated by the mannose-binding adhesin FimH located at the tip of bacterial pili. In a preliminary study, biphenyl α-D-mannopyranosides with an electron-withdrawing carboxylate on the aglycon were identified as potent FimH antagonists. Although passive permeability could be established by masking the carboxylate as an ester, insufficient solubility and fast hydrolysis did not allow to maintain the therapeutic concentration in the bladder for the requested period of time. By modifying the substitution pattern, mol. planarity and symmetry of the biphenyl aglycon could be disrupted leading to improved solubility In addition, when heteroatoms were introduced to the aglycon, antagonists with further improved solubility, metabolic stability as well as passive permeability were obtained. The best representative, the pyrrolylphenyl mannoside 42f exhibited therapeutic urine concentration for up to 6 h and is therefore a promising oral candidate for UTI prevention and/or treatment.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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: 1028-33-7, is researched, Molecular C13H20N4O2, about Influence of pentifylline on brain metabolism of normal and anoxic rats, the main research direction is pentifylline brain energy metabolism anoxia.Product Details of 1028-33-7.

SK-7 (pentifylline)(I) [1028-33-7] (25 mg/kg, orally) stimulated the energy metabolism of the brain in normal and anoxic rats resulting in increased levels of ATP [56-65-5], total adenine nucleotide pool, glycogen [9005-79-2], and pyridine nucleotides (NAD [53-84-9] and NADH2 [58-68-4]).

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-Hexyl-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione( cas:1028-33-7 ) is researched.Electric Literature of C13H20N4O2.Hassib, Sonia T. published the article 《Simultaneous determination of pentifylline and nicotinic acid by derivative spectrophotometry》 about this compound( cas:1028-33-7 ) in Egyptian Journal of Pharmaceutical Sciences. Keywords: pentifylline nicotinate determination derivative spectrophotometry. Let’s learn more about this compound (cas:1028-33-7).

First-derivative spectrophotometry with a zero-crossing technique of measurement was used for the quantitation of a mixture of pentifylline and nicotinic acid (4:1). Pentifylline was also evaluated in the presence of nicotinic acid by first and second-derivative modes applying peak-height measurement. Cosaldon Retard tablets were estimated for pentifylline and nicotinic acid in success using first-derivative mode.

The article 《Simultaneous determination of pentifylline and nicotinic acid by derivative spectrophotometry》 also mentions many details about this compound(1028-33-7)Electric Literature of C13H20N4O2, you can pay attention to it, because details determine success or failure

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Computed Properties of C7H6BrNO2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Methyl 6-bromonicotinate, is researched, Molecular C7H6BrNO2, CAS is 26218-78-0, about Enantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes. Author is Yang, Peng; Wang, Qiang; Cui, Bing-Hui; Zhang, Xiao-Dong; Liu, Hang; Zhang, Yue-Yuan; Liu, Jia-Liang; Huang, Wen-Yu; Liang, Ren-Xiao; Jia, Yi-Xia.

Enantioselective [3 + 2] annulation of N-heteroarenes such as 2-(2-bromophenyl)quinoline with alkynes R1CCR2 [R1 = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.; R2 = Me, Ph, benzyloxymethyl, (thiophen-2-ylmethoxy)methyl, etc.] has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand e.g., [(2R,3R)-3-(diphenylphosphanyl)butan-2-yl]diphenylphosphane and reducing reagent. A variety of electron-deficient N-heteroarenes e.g., 2-(2-bromophenyl)quinoline and internal or terminal alkynes are employed in this reaction, showing a broad substrate scope and good functionality tolerance. Annulation of electron-rich indoles I (R = H, 5-Cl) with alkynes is also developed. This protocol provides a straightforward access to a variety of N-spiroheterocyclic mols. such as II and in excellent enantioselectivities (76 examples, up to 99% ee).

After consulting a lot of data, we found that this compound(26218-78-0)Computed Properties of C7H6BrNO2 can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 26218-78-0, is researched, SMILESS is C1=NC(=CC=C1C(=O)OC)Br, Molecular C7H6BrNO2Journal, Heterocycles called Synthesis of pyrrolo[2,3-d]pyrimidine analogues: “”pyridine ring”” analogues of pemetrexed, Author is Xu, Yun; Yu, Mingfeng; Long, Yan; Wu, Han; Mao, Zhenmin, the main research direction is pyridine analog pemetrexed preparation anticancer.Category: tetrahydrofurans.

Two analogs of pemetrexed with its Ph ring replaced with a pyridine ring were synthesized as novel anticancer agents. Preliminary in-vitro evaluation indicated that replacement of the Ph moiety of pemetrexed by the pyridine ring with the 6-5 bicyclic ring system showed low cytotoxicity, that departs from the findings with antifolates bearing a 6-6 bicyclic system.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-Butan-2-ol(SMILESS: C[C@H](O)CC,cas:4221-99-2) is researched.Safety of 2-Amino-5-chlorobenzaldehyde. The article 《Interfacial acidity on oxide surfaces: a scaling paradigm and the role of the hydrogen bond》 in relation to this compound, is published in ChemRxiv. Let’s take a look at the latest research on this compound (cas:4221-99-2).

A fundamental understanding of acidity at an interface, as mediated by structure and mol.-surface interactions, is essential to elucidate the mechanisms of a range of chem. transformations. While the strength of an acid in the gas and solution phases is conceptually well understood, how acid-base chem. works at an interface is notoriously more complicated. Using d. functional theory and nonlinear vibrational spectroscopy, we have developed a method to determine the interfacial Bronsted-Lowry acidity of aliphatic alcs. adsorbed on the {100} surface of the model perovskite, strontium titanate. Here we show that, while shorter and less branched alkanols are less acidic as a gas and more acidic in solution, shorter alcs. are less acidic whereas less substituted alkanols are more acidic at the gas-surface interface. Hydrogen bonding plays a critical role in defining acidity, whereas structure-acidity relationships are dominated by van der Waals interactions between the alc. and the surface.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Safety of 2-Amino-5-chlorobenzaldehyde. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Amino-5-chlorobenzaldehyde, is researched, Molecular C7H6ClNO, CAS is 20028-53-9, about A facile one-pot synthesis of 2-substituted-3-aminoquinolines: preparation of benzo[b]naphthyridine-3-carbonitriles. Author is Wang, Yanong D.; Boschelli, Diane H.; Johnson, Steven; Honores, Erick.

A facile one-pot synthesis of 3-aminoquinolines from ortho-aminobenzaldehydes was developed. Et 6,7-dimethoxy-3-aminoquinoline-2-carboxylate, a key intermediate for the preparation of a 4-anilino-benzo[b][1,5]-naphthyridine-3-carbonitrile, was efficiently prepared by this method. Synthetic routes to 4-anilino-benzo[b][1,5]-naphthyridine-3-carbonitrile and 4-anilino-benzo[b][1,8]-naphthyridine-3-carbonitrile are described.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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: 20028-53-9, is researched, Molecular C7H6ClNO, about Process Development of CuI/ABNO/NMI-Catalyzed Aerobic Alcohol Oxidation, the main research direction is aerobic alc oxidation copper catalyst batch flow; aldehyde ketone preparation.Product Details of 20028-53-9.

An improved Cu/nitroxyl catalyst system for aerobic alc. oxidation has been developed for the oxidation of functionalized primary and secondary alcs. to aldehydes and ketones, suitable for implementation in batch and flow processes. This catalyst, which has been demonstrated in a >50 g scale batch reaction, addresses a number of process limitations associated with a previously reported (MeObpy)CuI/ABNO/NMI catalyst system (MeObpy = 4,4′-dimethoxy-2,2′-bipyridine, ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl, NMI = N-methylimidazole). Important catalyst modifications include the replacement of [Cu(MeCN)4]OTf with a lower-cost Cu source, CuI, reduction of the ABNO loading to 0.05-0.3 mol%, and use of NMI as the only ligand/additive (i.e., without a need for MeObpy). Use of a high flash point solvent, N-methylpyrrolidone, enables safe operation in batch reactions with air as the oxidant. For continuous-flow applications compatible with elevated gas pressures, better performance is observed with acetonitrile as the solvent.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem