Month: April 2022

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.VanAtta, Reuel B.; Franklin, Catherine C.; Valentine, Joan Selverstone researched the compound: Iron(III) trifluoromethanesulfonate( cas:63295-48-7 ).Application In Synthesis of Iron(III) trifluoromethanesulfonate.They published the article 《Oxygenation of organic substrates by iodosylbenzene catalyzed by soluble manganese, iron, cobalt, or copper salts in acetonitrile》 about this compound( cas:63295-48-7 ) in Inorganic Chemistry. Keywords: epoxidation olefin iodosylbenzene mechanism; metal nitrate triflate catalyst epoxidation. We’ll tell you more about this compound (cas:63295-48-7).

Reaction of PhIO with (Z)- (I) and (E)-stilbene (II), Me2C:CMe2 or cyclohexene in the presence of catalytic amounts of metal nitrates and triflates (metal = Fe2+, Fe3+, Mn2+, Cu2+) gave epoxidation in moderate to high yields. The same systems oxidize cumene to PhCMe2OH in moderate yields. All of the metal salt-PhIO reactions with II gave 16-86% I oxide, while reactions with I gave mixtures of II 0-82, I oxide 0-51%, and II oxide 4-51%. Some cleavage products were also observed Qual. comparisons of the epoxidation of the stilbenes catalyzed by M(O3SCF3)3 (M = Fe, Mn) with those catalyzed by the same metal porphyrins showed that the yields of the triflate- and porphyrin-catalyzed reactions were comparable for each metal ion. The triflates react more rapidly with II than with I, while the reverse was true for the porphyrins. Thus, the porphyrin ligand is not required for metal-ion catalysis of oxygenations of organic substrates by PhIO.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Quality Control of 1-(2-chloropyridine-4-yl)ethanone. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 1-(2-chloropyridine-4-yl)ethanone, is researched, Molecular C7H6ClNO, CAS is 23794-15-2, about Synthesis of some new 4-(2-chloropyridin-4-yl)-N-aryl-1,3-thiazol-2-amine derivatives as possible antifungal and antibacterial agents. Author is Narayana, B.; Raj, K. K. Vijaya; Ashalatha, B. V.; Kumari, N. Suchetha.

Novel 4-(2-chloropyridin-4-yl)-N-aryl-1,3-thiazol-2-amines were prepared by reacting (4-bromoacetyl)-2-chloropyridine with thiourea and substituted thioureas. The newly synthesized compounds were characterized by anal. and spectral data. All the compounds were screened for their antifungal and antibacterial activities. Almost all the compounds possess excellent antifungal and antibacterial activities.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Angewandte Chemie, International Edition called Alkylation-Terminated Catellani Reactions Using Alkyl Carbagermatranes, Author is Jiang, Wei-Tao; Xu, Meng-Yu; Yang, Shuo; Xie, Xiu-Ying; Xiao, Bin, which mentions a compound: 175136-62-6, SMILESS is FC(C1=CC(C(F)(F)F)=CC(P(C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)C3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)=C1)(F)F, Molecular C24H9F18P, Quality Control of Tris(3,5-bis(trifluoromethyl)phenyl)phosphine.

The Catellani reaction has received substantial attention because it enables rapid multiple derivatization on aromatics While using alkyl electrophiles to achieve ortho-alkylation was one of the earliest applications of the Catellani reaction, ipso-alkylation-terminated reactions with β-H-containing reactants has not been realized to date. Herein, we report alkylation-terminated Catellani reaction using alkyl carbagermatranes (abbreviated as alkyl-Ge) as nucleophiles. The reactivity of alkyl-Ge and alkyl-B(OH)2 in this reaction is discussed. This approach enables efficient dialkylation with β-H-containing reactants, which was previously inaccessible by Catellani reactions.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Damavandi, Saman; Sandaroos, Reza published the article 《Solvent-free one-pot synthesis of indenoquinolinones catalyzed by iron(III) triflate》. Keywords: aminonaphthalene aminoanthracene aldehyde indandione cyclocondensation iron triflate catalyst; indenoquinolinone preparation green chem.They researched the compound: Iron(III) trifluoromethanesulfonate( cas:63295-48-7 ).Electric Literature of C3F9FeO9S3. 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:63295-48-7) here.

A green three-component one-pot condensation synthesis of 16 indenoquinolinone from aromatic aldehydes, 1-aminonaphthalene or 1-aminoanthracene and 1,3-indandione catalyzed by Fe(OTf)3 was described. The isolated yields ranged from 80% to 92%.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The action of thiourea on α,β-dibromopropionic acid》. Authors are Biilmann, Einar; Pedersen, E. Egelund.The article about the compound:2,3-Dibromopropionic acidcas:600-05-5,SMILESS:O=C(O)C(Br)CBr).Name: 2,3-Dibromopropionic acid. Through the article, more information about this compound (cas:600-05-5) is conveyed.

CS(NH2)2 (I) added to BrCH2CHBrCO2H (II) gave crystals whose analysis corresponds to the sum of 2 mols. of I and 1 of II minus 1 mol. H2O. The structure CO.NH.C(:NH).S.CHCH2SC(NH2)(:NH).2HBr is suggested.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Iron(III) trifluoromethanesulfonate(SMILESS: O=S(C(F)(F)F)([O-])=O.O=S(C(F)(F)F)([O-])=O.O=S(C(F)(F)F)([O-])=O.[Fe+3],cas:63295-48-7) is researched.Synthetic Route of C10H7F2N3O. The article 《The First 1,3,4-Oxadiazole Based Dinuclear Iron(II) Complexes Showing Spin Crossover Behavior with Hysteresis》 in relation to this compound, is published in European Journal of Inorganic Chemistry. Let’s take a look at the latest research on this compound (cas:63295-48-7).

Three new dinuclear complexes [FeII2(μ-L)2]X4 (L is the bis-tridentate ligand 2,5-bis{[(2-pyridylmethyl)amino]methyl}-1,3,4-oxadiazole and X = ClO4-, BF4- and CF3SO3-) were synthesized and fully characterized by single-crystal x-ray diffraction, Mossbauer spectroscopy and magnetic susceptibility measurements. Upon cooling, a trapped [high-spin-low-spin] state of the iron(II) centers was detected. Depending on the counterion, a pronounced thermal hysteresis is found. In one case, it was possible to observe a space group change that accompanies the spin transition. This is the first system showing spin crossover based on an oxadiazole ligand.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Yao, Huifang; Liu, Yong; Tyagarajan, Sriram; Streckfuss, Eric; Reibarkh, Mikhail; Chen, Kuanchang; Zamora, Ismael; Fontaine, Fabien; Goracci, Laura; Helmy, Roy; Bateman, Kevin P.; Krska, Shane W. researched the compound: Tris(3,5-bis(trifluoromethyl)phenyl)phosphine( cas:175136-62-6 ).Name: Tris(3,5-bis(trifluoromethyl)phenyl)phosphine.They published the article 《Enabling Efficient Late-Stage Functionalization of Drug-Like Molecules with LC-MS and Reaction-Driven Data Processing》 about this compound( cas:175136-62-6 ) in European Journal of Organic Chemistry. Keywords: late stage drug functionalization LCMS automated reaction data processing. We’ll tell you more about this compound (cas:175136-62-6).

Late-stage functionalization (LSF) through C-H functionalization of drug leads is a powerful synthetic strategy for drug discovery. A key challenge in LSF is that multiple regioisomeric products are often generated, which requires slow and laborious product isolation and structure confirmation steps. To address this, an anal. approach using LC-HR-MS/MS coupled with automated chem. aware data processing was developed. Using this method to analyze reaction screening arrays based on three common C-H functionalization chemistries with a set of marketed drugs, the relative amount and localization of chem. modification could be determined for each regioisomeric product generated in the screening. This approach allows one to construct a workflow in which the various regioisomeric products of a given transformation are triaged according to their site of modification, allowing downstream isolation and structure elucidation efforts to focus on those analogs of highest interest, leading to an overall increase in productivity of the LSF strategy.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – 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: 23794-15-2, is researched, Molecular C7H6ClNO, about Synthesis of some biologically active 2,4′-bipyridine-5-carbonitriles carrying the 4-hydroxyphenylthio moiety, the main research direction is bipyridine carbonitrile hydroxyphenylthio preparation antibacterial fungicide structure activity relationship.Reference of 1-(2-chloropyridine-4-yl)ethanone.

The reaction of 4-hydroxythiophenol with 4-acetyl-2-chloropyridine yielded a key intermediate, 1-{2-[(4-hydroxyphenyl)thio]pyridin-4-yl}ethanone. Further treatment of the key intermediate with Et cyanoacetate and various aromatic aldehydes in the presence of ammonium acetate furnished 4-aryl-2′-[(4-hydroxyphenyl)thio]-6-oxo-1,6-dihydro-2,4′-bipyridine-5-carbonitriles, e.g., I (R = H, MeO, Ph, Cl, Me2N). On the other hand, condensation of the key intermediate with aromatic aldehydes and malononitrile in the presence ammonium acetate of in alc. gave 6-amino-4-aryl-2′-[(4-hydroxyphenyl)thio]-2,4′-bipyridine-5-carbonitriles. All the title compounds were subjected to in vitro antibacterial testing against two strains and antifungal screening against two fungi. Some of the compounds showed promising activity.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2,3-Dibromopropionic acid, is researched, Molecular C3H4Br2O2, CAS is 600-05-5, about Additions of halogen by means of N-bromosuccinimide. III. Preparation of aliphatic α,β-dihalo carboxylic acids, the main research direction is ALIPHATIC DIHALO CARBOXYLIC ACID; DIHALO CARBOXYLIC ACID ALIPHATIC; CARBOXYLIC ACID ALIPHATIC DIHALO.Reference of 2,3-Dibromopropionic acid.

cf. CA 64, 11114f. α-Bromo-β-chlorocarboxylic acids and their esters were readily obtained from the corresponding α,β-unsaturated carboxylic acids with N-bromosuccinimide (I) and HCl. The position of the halogen atoms was confirmed by partial hydrolysis of the products. The appropriate α,β-unsaturated carboxylic acid or ester (0.1 mole), 50 cc. 3N HCl, and 50 cc. Et2O treated with stirring at -6° during 40 min. with 17.8 g. I in portions and filtered, and the aqueous phase diluted with 60 cc. saturated aqueous NaCl and extracted 8 hrs. with Et2O yielded the corresponding α-bromo-β-chloro derivative By this method were prepared from the appropriate α,β-unsaturated compounds the following α-bromo-β-chloro derivatives (m.p. or b.p./ mm. and % yield given): ClCH2CHBrCO2H (II), 43°, 61; Et ester of II, 93°/20 (81°/10), 70; ClCH2CMeBrCO2H (III), 43° (125°/14), 78.5; Me ester of III, 87°/24 (69°/9), 69; MeCHClCHBrCO2H, 70° (143°/25, 123°/8), 73. CH2:CHCO2H with I and HBr gave similarly 50% BrCH2CHBrCO2H, m. 51°. The appropriate α-bromo-β-chlorocarboxylic acid (0.002 mole) in 15 cc. Me2CO and 5 cc. H2O kept 3 days at room temperature gave the corresponding β-hydroxy-α-bromocarboxylic acid. In this manner were prepared HOCH2CHBrCO2H, 71% MeCH(OH)CHBrCO2H, m. 86-7°, and 70% HOCH2CMeBrCO2H, m. 107-8°.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Tris(3,5-bis(trifluoromethyl)phenyl)phosphine, is researched, Molecular C24H9F18P, CAS is 175136-62-6, about Synthesis and Application of 2,6-Bis(trifluoromethyl)-4-pyridyl Phosphanes: The Most Electron-Poor Aryl Phosphanes with Moderate Bulkiness, the main research direction is fluoromethylpyridylphosphine preparation steric effect Taft molybdenum rhodium catalyst; optimized mol structure Stille vinyltin transmetalation palladium fluoromethylpyridylphosphine DFT; Stille ketone addition arylboronic asym arylation tosylimine catalyst fluoromethylpyridylphosphine.Quality Control of Tris(3,5-bis(trifluoromethyl)phenyl)phosphine.

BFPy (BFPy = 2,6-bis(trifluoromethyl)-4-pyridyl) phosphines mimic the electronic and steric characters of P(C6F5)3 and PPh3, resp. These novel ligands showed a large ligand acceleration effect on Stille coupling, the Rh-catalyzed 1,2-addition of arylboronic acids to unactivated ketones and the asym. arylation of N-tosylimine using phenylboronic acid. Particularly in the last two cases, the BFPy phosphine achieved the record of the highest catalytic activity. The Stille coupling of iodobenzene with tributyl(vinyl)stannane in the presence of [Pd2[dba]3] (dba = dibenzylideneacetone) and P(BFPy)3 (1a) in THF gave styrene in 94% yield. The ligand effect in transmetalation of the vinyl group to Pd was evaluated by DFT calculations of the reaction of [L(Ph)PdI] (L = 1a, PPH3, AsPh3) with (vinyl)SnMe3. The BFPy phosphine ligand accelerated the Rh-catalyzed 1,2-addition of arylboronic acids to unactivated ketones. Reaction of five ketones with five arylboronic acids in the presence of [{RhOH(cod)}2] (cod = 1,5-cyclooctadiene) and biphenyl (±)-(6-MeO-2-P(BFPy)2C6H3)2 ((±)-3a) afforded the corresponding tert-alcs. in 81% to 99% yield. E.g., reaction of 4-trifluoromethylacetophenone with phenylboronic acid gave 1-phenyl-1-(4-trifluoromethylphenyl)ethanol in 99% yield. Highly enantioselective catalysis using (R)-3a was achieved in the asym. arylation of arylimine 4-MeOC6H4C(H):NTs (13, Ts = tosyl) with phenylboronic acid. The reaction of tosylimine 13 with one equivalent phenylboronic acid in the presence of [{RhCl(C2H4)2}2] and (R)-3a gave N-tosylamine (S)-4-MeOC6H4C(H)(Ph)N(H)Ts in 98% yield and 98% ee.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem