Month: October 2022

Severance, Rachel C.; Ellsworth, Joe; Smith, Mark D.; Kelley, Jennifer; Peterson, LeRoy Jr.; zur Loye, Hans-Conrad published their research in Journal of Chemical Crystallography on December 31 ,2010. The article was titled 《Synthesis and Crystal Structure of the Coordination Complex Cu(ppca’)2(H2O)2 (ppca’ = 3,4′-Bipyridine-6-Carboxylic Acid)》.Formula: C11H8N2O2 The article contains the following contents:

The coordination complex Cu(ppca’)2(H2O)2 (1) was synthesized hydrothermally using the ligand 3,4′-bipyridine-6-carboxylic acid (ppca’). Complex 1 consists of pseudo-octahedral copper(II) units hydrogen bonded into a three-dimensional network that crystallizes in the monoclinic P21/n space group. In complex 1, a 5.3429(4), b 29.343(2), c 6.7940(5) Å, and β 110.635(2)°. The experimental part of the paper was very detailed, including the reaction process of [3,4′-Bipyridine]-6-carboxylic acid(cas: 1214363-66-2Formula: C11H8N2O2)

[3,4′-Bipyridine]-6-carboxylic acid(cas: 1214363-66-2) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Formula: C11H8N2O2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Bromination of methylpyridines in fuming sulfuric acid》 were Does, L. van der; Hertog, H. J.. And the article was published in Recueil des Travaux Chimiques des Pays-Bas in 1965. Safety of 2,3,5-Tribromo-4-methylpyridine The author mentioned the following in the article:

Methylpyridines heated and shaken with Br and H2SO4 produce a mixture of mono and polybromomethyl derivatives A tube was charged with 18.6 g. 2-picoline (I), 100 ml. fuming H2SO4 containing 65% SO3, and 12.8 Br and sealed. The contents were heated at 80° for 7 hrs. with shaking. On cooling 5-bromo-2-picoline (II) [m. 32-3°; HgCl2 adduct m. 189-91° (alc.)] sep. The residue [a mixture of II and 3-bromo-2-picoline (III)] is converted to 5-amino-2-picoline [m. 95-6° (petroleum ether)] and 3-amino-2-picoline in 84% yield. Bromination of 18.6 g. I at 130° gives 20 g. of a mixture of II and III and 3.6 g. of a residue which on steam distillation yields 0.8 g. 3,5,6-tribromo-2-picoline, m. 76-7° (alc.). No dibromopicolines were found. Bromination of 18.6 g. 3-picoline at 80° yields 5.2 g. 5-bromo-3-picoline (IV) (m. 16.5-7°), 2,4 g. 2-bromo-3-picoline, 0.4 g. 6-bromo-3-picoline, and 7.2 g. 2,5-dibromo-3-picoline (V) (m. 41-2°), separated by preparative gas liquid chromatography. IV us converted to 5-amino-3-picoline [m. 61-3° (petroleum ether); picrate m. 225° (decomposition)] in 90% yield. V is identified by comparing it with an authentic sample prepared from 2-amino-5-bromo-3-picoline [m. 90-2° (petroleum ether)] with 48% HBr in 70% yield. Bromination of 18.6 g. 4-picoline (VI) at 80° yields 17 g. 3-bromo-4-picoline (VII) [b9 74-5° nD 1.5610; HgCl2 adduct, m. 175-7° (alc.)], 3,5-dibromo-4-picoline (VIII) [m. 104-7°; HgCl2 adduct m. 219-21° (alc.)], and 0.03 g. 2,3,5-tribromo-4-picoline (IX) [m. 56-7° (aqueous alc.)]. No 2,5-dib0romo-4-picoline [m. 37-8° (alc.)] was found. Bromination of 0.15 mole VI at 90° gives 0.06 mole VIII and 0.03 mole IX. VII, heated with aqueous NH3 and CuSO4.5H2O in a sealed tube at 135° for 50 hrs., gives 3-amino-4-picoline (m. 106-7°; picrate m. 177-8°) in 85% yield. The structure of IX was proved by preparing it from 2-amino-3,5-dibromo-4-picoline [m. 123-4° (aqueous alc.)] with HBr. IX is converted to 3,5-dibromo-2-hydrazino-4-picoline (X) [m. 151-2° (alc.)] in 65-70% yield by heating with N2H4.H2O in 96° aqueous alc. at 130° for 5 hrs. in a sealed tube. X, when refluxed 4 hrs. with 10% aqueous CuSO4 solution, converts to VIII (30% yield), thus proving its structure. Bromination of 32.1 g. 2,6-lutidine (XI) at 55° for 5 hrs. produces 12 g. 3-bromo-2,6-lutidine [b14 82.5-3°, n2D0 1.5598; picrate m. 148-50° (alc.)] which can be converted to 3-amino-2,6-lutidine (m. 122°) to prove its structure. Bromination of 15.9 g. XI at 90° for 7 hrs. produces 32.8 g. crude 3,5-dibromo-2,6-lutidine (m. 46-57°) on steam distillation (m.p. of pure compound is 64°). Ionic mechanism for the bromination is postulated. The influence of Me groups in orientation is seen as less than that of the NH2 group. In the experiment, the researchers used many compounds, for example, 2,3,5-Tribromo-4-methylpyridine(cas: 3430-25-9Safety of 2,3,5-Tribromo-4-methylpyridine)

2,3,5-Tribromo-4-methylpyridine(cas: 3430-25-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Safety of 2,3,5-Tribromo-4-methylpyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Double Deprotonation of Pyridinols Generates Potent Organic Electron-Donor Initiators for Haloarene-Arene Coupling》 were Barham, Joshua P.; Coulthard, Graeme; Kane, Ryan G.; Delgado, Nathan; John, Matthew P.; Murphy, John A.. And the article was published in Angewandte Chemie, International Edition in 2016. Reference of Methyl 5-methoxypicolinate The author mentioned the following in the article:

Transition metal-free couplings of haloarenes with arenes, triggered using alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently it was reported that 2-pyridinecarbinol (11) extends the reaction to aryl bromides. This paper studies the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron-poor benzoyl derivatives can be transformed into electron donors to initiate these reactions. In addition to this study using Methyl 5-methoxypicolinate, there are many other studies that have used Methyl 5-methoxypicolinate(cas: 29681-39-8Reference of Methyl 5-methoxypicolinate) was used in this study.

Methyl 5-methoxypicolinate(cas: 29681-39-8) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Reference of Methyl 5-methoxypicolinate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Pyrimidines. XLIII. Ring transformations in reactions of heterocyclic compounds with nucleophiles. IX. Conversion of N-methylpyrimidinium salts to pyridines by carbanions》 were Oostveen, E. A.; Van der Plas, H. C.. And the article was published in Recueil des Travaux Chimiques des Pays-Bas in 1974. Reference of 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid The author mentioned the following in the article:

On treatment with active methylene compounds in basic media the quaternary pyrimidinium salts were converted into pyridine derivatives. Thus, I(R = R1 = H; R = Ph, R1 = H, R = H, R1 = Ph) and CH2(CO2Et) with NaOH gave II. In the experiment, the researchers used many compounds, for example, 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid(cas: 10177-08-9Reference of 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid)

2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid(cas: 10177-08-9) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Reference of 2-Oxo-5-phenyl-1,2-dihydropyridine-3-carboxylic acid Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Otero-Fraga, Jorge; Suarez-Pantiga, Samuel; Montesinos-Magraner, Marc; Rhein, Dennis; Mendoza, Abraham published 《Direct and Stereospecific [3+2] Synthesis of Pyrrolidines from Simple Unactivated Alkenes》.Angewandte Chemie, International Edition published the findings.Product Details of 31106-82-8 The information in the text is summarized as follows:

Pyrrolidines are important heterocyclic compounds with endless applications in organic synthesis, metal catalysis, and organocatalysis. Their potential as ligands for first-row transition-metal catalysts inspired a new method to access complex poly-heterocyclic pyrrolidines in one step from available materials. This fundamental step forward is based on the discovery of an essential organoaluminum promoter that engages unactivated and electron-rich olefins in intermol. [3+2] cycloadditions In the experimental materials used by the author, we found 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Product Details of 31106-82-8)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. Pyridines form stable salts with strong acids. Pyridine itself is often used to neutralize acid formed in a reaction and as a basic solvent. Product Details of 31106-82-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Van Raden, Jeff M.; Louie, Shayan; Zakharov, Lev N.; Jasti, Ramesh published 《2,2′-Bipyridyl-Embedded Cycloparaphenylenes as a General Strategy To Investigate Nanohoop-Based Coordination Complexes》.Journal of the American Chemical Society published the findings.SDS of cas: 53939-30-3 The information in the text is summarized as follows:

Because of their unique cyclic architectures, tunable electronic properties, and supramol. chemistries, cycloparaphenylenes (CPPs) have the potential to act as a new class of ligands for coordination cages, metal-organic frameworks, and small-mol. transition-metal complexes. However, currently there is no general strategy to coordinate the cyclic framework to a variety of metal centers. The authors report here a general and scalable synthetic strategy to embed 2,2′-bipyridine units into the backbone of CPPs. The authors use this approach to synthesize a 2,2′-bipyridine-embedded [8]CPP (L), which the authors show can successfully coordinate to both Pd(II) and Ru(II) forming [PdLCl2], [PdL2](BF4)2 and [Ru(L)(bipy)2](PF6)2. The resulting coordination complexes, a Pd(II) nanohoop dimer and a bis(bipyridyl)ruthenium(II) functionalized nanohoop, show unique solid-state and photophys. properties. This work provides a proof of concept for a general strategy to use nanohoops and their derivatives as a new class of ligands. The experimental part of the paper was very detailed, including the reaction process of 5-Bromo-2-chloropyridine(cas: 53939-30-3SDS of cas: 53939-30-3)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. SDS of cas: 53939-30-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Shu, Bing; Cao, Jiaojiao; Kuang, Guotao; Qiu, Jun; Zhang, Meiling; Zhang, Yan; Wang, Mingxue; Li, Xiaoya; Kang, Shuangshuang; Ou, Tian-Miao; Tan, Jia-Heng; Huang, Zhi-Shu; Li, Ding published 《Syntheses and evaluation of new acridone derivatives for selective binding of oncogene c-myc promoter i-motifs in gene transcriptional regulation》.Chemical Communications (Cambridge, United Kingdom) published the findings.Formula: C7H9NO The information in the text is summarized as follows:

We synthesized a series of acridone derivatives for specific binding ligands of i-motifs. Subsequent evaluations showed that B19 (I) could selectively bind to and stabilize the c-myc promoter i-motif without significant binding to the G-quadruplex and duplex DNA. This caused down-regulation of c-myc transcription and expression, resulting in tumor cell apoptosis. In the part of experimental materials, we found many familiar compounds, such as 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Formula: C7H9NO)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine and its simple derivatives are stable and relatively unreactive liquids, with strong penetrating odours that are unpleasant.Formula: C7H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Indian Journal of Heterocyclic Chemistry included an article by Bhasker, G. Vijaya; Satyanarayana, G. V.; Laxminarayana, E.; Latha, A.; Chary, M. Thirumala. Computed Properties of C5H5BrN2. The article was titled 《Synthesis, antibacterial activity, and docking studies of some new 2-substituted-1,8-naphthyridine derivatives》. The information in the text is summarized as follows:

Two series of novel 2-substituted-1,8-naphthyridine derivatives I (R = quinolin-3-yl, 4-AcC6H4, 2-Br-5-pyridyl, etc.) and II (R = quinolin-3-yl, 4-Cl-2-pyridyl, 2-BrC6H4) were synthesized. These compounds were evaluated for their antibacterial activity. Docking studies for these title compounds are also presented in this communication. In the part of experimental materials, we found many familiar compounds, such as 6-Bromopyridin-3-amine(cas: 13534-97-9Computed Properties of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Computed Properties of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Journal of the American Chemical Society included an article by MacQueen, Preston M.; Tassone, Joseph P.; Diaz, Carlos; Stradiotto, Mark. Synthetic Route of C7H9NO. The article was titled 《Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols》. The information in the text is summarized as follows:

The use of (L)Ni(o-tolyl)Cl precatalysts (L = PAd-DalPhos or CyPAd-DalPhos, I or II, resp.) enables the C(sp2)-O cross-coupling of primary, secondary, or tertiary aliphatic alcs. with (hetero)aryl electrophiles, including unprecedented examples of such nickel-catalyzed transformations employing (hetero)aryl chlorides, sulfonates, and pivalates. In addition to offering a competitive alternative to palladium catalysis, this work establishes the feasibility of utilizing ancillary ligation as a complementary means of promoting challenging nickel-catalyzed C(sp2)-O cross-couplings, without recourse to precious-metal photoredox catalytic methods.2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Synthetic Route of C7H9NO) was used in this study.

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. When pyridine is adsorbed on oxide surfaces or in porous materials, the following species are commonly observed: (i) pyridine coordinated to Lewis acid sites, (ii) pyridine H-bonded to weakly acidic hydroxyls, and (iii) protonated pyridine. At high coverage, physisorbed pyridine and protonated dimers can also be observed.Synthetic Route of C7H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2019,Chemical Communications (Cambridge, United Kingdom) included an article by Xu, Rui; Cai, Chun. Synthetic Route of C33H24IrN3. The article was titled 《Three-component difluoroalkylation-thiolation of alkenes by iron-facilitated visible-light photoredox catalysis》. The information in the text is summarized as follows:

An efficient synthesis of(arylthio)difluoroalkanoates R1SCHR2CHR3CF2CO2Et [R1 = 4-MeC6H4, 4-FC6H4, PhCH2, 2-pyridinyl, 2-pyrimidinyl, etc.; R2 = n-hexyl, Ph, 4-MeOC6H4, etc., R3 = H; R2R3 = (CH2)3] has been developed via three-component difluoroalkylation-thiolation of alkenes R2CH:CHR3 with thiols R1SH and Et difluorobromoacetate using iron-facilitated visible light photoredox catalysis. The Csp3-Csp3 and Csp3-S bonds were simultaneously constructed smoothly under mild conditions. The reaction exhibits a broad substrate scope of alkenes and thiols with good to excellent yields. In the experiment, the researchers used fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6Synthetic Route of C33H24IrN3)

fac-Tris(2-phenylpyridine)iridium(cas: 94928-86-6) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Synthetic Route of C33H24IrN3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem