Month: April 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《The chlorination of methyl derivatives of pyridine. Part I. 2-Methylpyridine》. Authors are Sell, William James.The article about the compound:3,4,5-Trichloropyridinecas:33216-52-3,SMILESS:C1=NC=C(C(=C1Cl)Cl)Cl).Recommanded Product: 3,4,5-Trichloropyridine. Through the article, more information about this compound (cas:33216-52-3) is conveyed.

Based on the basic character of trichloropyridine, chlorine atoms may occupy the positions 3, 4, 5, and thus, experimental verification of this assumption was carried out. The substance 3:4:5-trichloro-2-aminopyridine was used for comparison. This compound should be obtained from the trichloropicolinic acid by converting it into its amide, and the latter by the Hoffmann reaction into the 3:4:5-trichloro-2-aminopyridine. Chlorine had no reactions the ordinary temperature, even in the presence of chlorine carriers as iodine or ferric chloride. However, when temperature of the hydrochloride was increased to 100°, fumes of hydrochloride were formed. As the chlorination proceeded, a heavy layer was formed in the liquid, which increased in quantity until the upper layer disappeared and no increase in weight occurred. At > 130°, a good deal of trichloropicolinic acid was decomposed into trichloropyridine, which remained in solution in sulfuric acid. Samples of the double salts with mercuric chloride from the different sources showed identical melting points and general characteristics. Traces of crystalline product was observed during the steam-distillation, and when recrystallized from an alcohol, it formed a mass of fine needles melting at 160°-161°.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

SDS of cas: 286014-53-7. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 1,3-Dimesityl-1H-imidazol-3-ium tetrafluoroborate, is researched, Molecular C21H25BF4N2, CAS is 286014-53-7, about Enantioselective cooperative proton-transfer catalysis using chiral ammonium phosphates. Author is Zhang, Linrui; Yuan, Pengfei; Chen, Jiean; Huang, Yong.

Chiral phosphorate anions are shown to be highly enantioselective templates for proton-transfer catalysis. A salt generated in situ from a bridgehead amine and a BINOL-derived chiral phosphoric acid serves as an effective proton-shuttle that exhibits remarkable enantioselectivity in a bioinspired, triple co-operative catalysis involving an achiral NHC. Thioesters with a β-chiral center can be prepared in a single step from substituted cinnamaldehyde derivatives, with up to 99% yield and 99% ee. Heteroaryl groups are well tolerated in these reactions, despite the presence of basic sites.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

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, Research Support, Non-U.S. Gov’t, Angewandte Chemie, International Edition called Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation, Author is Delcaillau, Tristan; Bismuto, Alessandro; Lian, Zhong; Morandi, Bill, which mentions a compound: 17696-11-6, SMILESS is O=C(O)CCCCCCCBr, Molecular C8H15BrO2, Recommanded Product: 17696-11-6.

A nickel-catalyzed aryl thioether metathesis was developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Safety of 7-Chloro-4-(piperazin-1-yl)quinoline. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 7-Chloro-4-(piperazin-1-yl)quinoline, is researched, Molecular C13H14ClN3, CAS is 837-52-5, about Synthesis of Novel G Factor or Chloroquine-Artemisinin Hybrids and Conjugates with Potent Antiplasmodial Activity. Author is Pepe, Dionissia A.; Toumpa, Dimitra; Andre-Barres, Christiane; Menendez, Christophe; Mouray, Elisabeth; Baltas, Michel; Grellier, Philippe; Papaioannou, Dionissios; Athanassopoulos, Constantinos M..

A series of novel hybrids of artemisinin (ART) with either a phytormone endoperoxide G factor analog (GMeP) or chloroquine (CQ) and conjugates of the same compounds with the polyamines (PAs), spermidine (Spd), and homospermidine (Hsd) were synthesized and their antiplasmodial activity was evaluated using the CQ-resistant P. falciparum FcB1/Colombia strain. The ART-GMeP hybrid I and compounds II [n = 1, 2] which are conjugates of Spd and Hsd with two mols. of ART and one mol. of GMeP, were the most potent with IC50 values of 2.6, 8.4, and 10.6 nM, resp. The same compounds also presented the highest selectivity indexes against the primary human fibroblast cell line AB943 ranging from 16,372 for the hybrid I to 983 for the conjugate II [n = 2] of Hsd.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

SDS of cas: 33216-52-3. 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. Compound: 3,4,5-Trichloropyridine, is researched, Molecular C5H2Cl3N, CAS is 33216-52-3, about Structure of products of chlorination of α-picoline.

The structures of the title products were determined by EPR, NMR, and mass spectroscopy. Isolated were 3,5-dichloro-, 3,4,5-trichloro-, 2,3,4,5-tetrachloro-, and pentachloropyridine, and I-IV; there was no V in the reaction mixture

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Utilization of β-oxo diesters in the synthesis of β-diketone esters》. Authors are Gelin, Rene; Gelin, Suzanne; Poimboeuf, Jean Glaude.The article about the compound:Ethyl 3-Ethoxy-2-Propenoatecas:1001-26-9,SMILESS:O=C(OCC)/C=C/OCC).Synthetic Route of C7H12O3. Through the article, more information about this compound (cas:1001-26-9) is conveyed.

β-Oxo diesters, EtO2C(CH2)nCO CH2CO2Et, (I), synthesized by a new rapid method (CA 61, 4209c) were converted into ethoxymagnesium derivatives, which on reaction with various acid chlorides yielded α-acyl β-oxodiesters EtO2C(CH2)nCOCH(COR)CO2Et (II). On decarboxylation (loc. cit.) these yielded the β-diketone esters, EtO2C(CH2)n,COCH2COR (III). III gave cupric derivatives which were utilized in purification They showed an intense ir absorption at 1610 cm.-1 (enolized β-diketone).

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《[Haloderivatives of] pyridine[carboxylic acids]》. Authors are Dohrn, M.; Diedrich, P..The article about the compound:3,4,5-Trichloropyridinecas:33216-52-3,SMILESS:C1=NC=C(C(=C1Cl)Cl)Cl).Category: bromides-buliding-blocks. Through the article, more information about this compound (cas:33216-52-3) is conveyed.

3,5-Diiodochelidamic acid (I) [chloride, m. 149°; Me, m. 173°, Et (II), m. 169°, and benzyl, m. 200° (decomposition), esters] and Me2SO4 in aqueous KOH at 35° give 3,5-diiodo-N-methylchelidamic acid (III), m. 174° (decomposition) (Me ester, m. 194-5% while the Ag salt of II and Mel in xylene afford the Et ester, m. 100-1°, of 3,5-diiodo O-methylchelidamic (3,5-diiodo-4-methoxypyridine-2,6-dicarboxylic) acid, decomposes 176°. 3,5-Diiodo-4-ethoxy-, m. 174° (decomposition) (Me ester, m. 131°), -propoxy-, m. 156° (decomposition) (Me ester, m. 89°), -butoxy-, m. 145° (decomposition) (Me ester, m. 82°), and benzyloxy-, m. 167° (decomposition) (Me ester, m. 120°), -pyridine-2,6-dicarboxylic acids are prepared similarly. III heated at 170° gives 3,5-diiodo-N-methyl-4-pyridone, M. 214-5°, also prepared from 3,5-diiodo-4-pyridone (IV), m. 321° (decomposition), and Me2SO4 in aqueous KOH; IV is obtained from 4-pyridone and ICl in dilute HCl and by hydrolysis of its N-Ac derivative, m. 245° (decomposition) [from I and boiling AC2O]. I and IV with ClSO3H give the corresponding N-sulfo derivatives, m. 210° (decomposition) and 183° (decomposition), resp., hydrolyzed by H2O to H2SO4 and I and IV. 3,5-Diiodo-4-pyridone-N-acetic acid, m. 240° (decomposition), is prepared from IV and CH2ClCO2H. 4-Pyridone-2-carboxylic acid (V) and I in aqueous KOH give the 3,5-di-I derivative, decomposes 250° [N-Me, m. 159° (decomposition), and NCH2CO2H, m. 223° (decomposition), derivatives]; 2-pyridone-6-carboxylic acid similarly affords the 3,5-di-I derivative, decomposes 272° [N-Me derivative, m. 194° (decomposition)], also formed by iodination of 2-pyridone-5,6-dicarboxylic acid. 3,5-Dichloro-, m. above 300° (N-Me derivative, m. 166°), and 3,5-dibromo-, m. above 300° [N-Me derivative, m. 170° (decomposition)], -4-pyridone-2-carboxylic acids are obtained by halogenation of V. Et 3,5-dichlorochelidamate, m. 96°, and PCl5, give the Et ester, m. 35°, of 3,4,5-trichloropyridine-2,6-dicarboxylic acid, decomposes 150°. 4-Chloro-, m. 232° (decomposition) (Et ester, m. 111°), and 4-bromo-, m. 186° (decomposition) (Et ester, m. 98-9°), -3,5-diiodopyridine-2,6-dicarboxylic acids are prepared from II and PCl5 + POCl3 and PBr5, resp. The Et ester of 3,4,5-tri-bromopyridine-2,6-dicarboxylic acid (m. 180° (decomposition)) m. 67°. 3,4,5-Trichloropyridine, m. 76-7°, from 3,5-dichloro-4-pyridone, PCl5, and POCl3, at 125°, with EtOH-KHS gives 3,5-dichloro-4-thiolpyridine, m. 188°, oxidized by alk. KMnO4 to 3,5-dichloro-pyridine-4-sulfonic acid, m. above 300°. 4-Chloro-3,5-dibromo-, m. 98°, and 4-chloro 3,5-diiodo-, m. 175°, -pyridines are similarly converted by way of 3,5-dibromo-, m. 222°, and 3,5-diiodo-, m. 206° (decomposition), -4-thiolpyridines into 3,5-dibromo- (VI) and 3,5-diiodo- (VII), decompose 308°, -pyridine-4-sulfonic acids. 3,5-Dibromo- and 3,5-diiodopyridine-2-sulfonic acids, both decompose above 300°, are prepared similarly. VI and aqueous NH3 (d. 0.91) at 130° give 3,5-dibromo-4-aminopyridine, m. 169-70°;3,5-dibromo-4-anilino-, m. 167°, and -4-o-carboxyanilino-, m. 252° (as Et ester, m. 105-6°), -pyridines are formed with PhNH2 and o-NH2C6H4.CO2Et, resp. When an aqueous solution of VI is heated, 3,5,3′,5′-tetrabromo-N-4′-pyridyl-4-pyridone, m. above 300°, and SO2 are formed. 3,5,3′,5′-Tetraiodo-N-4′ -pyridyl-4-pyridone, decomposes above 300°, is obtained similarly from VII.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of C9H8BrN. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6-Bromo-3-methyl-1H-indole, is researched, Molecular C9H8BrN, CAS is 1219741-50-0, about Chalcogen-Chalcogen Bonding Catalysis Enables Assembly of Discrete Molecules. Author is Wang, Wei; Zhu, Haofu; Liu, Shuya; Zhao, Zhiguo; Zhang, Liang; Hao, Jingcheng; Wang, Yao.

Despite the observation of noncovalent interactions between chalcogen atoms in X-ray crystal structures, catalysis that harnesses the power of such chalcogen-chalcogen bonding interactions to produce advanced mols. remains an unresolved problem. Here, we show that a class of extraordinary chalcogen-bonding catalysts enables assembly of discrete small mols. including three β-ketoaldehydes and one indole, leading to the construction of N-heterocycles in a highly efficient manner. The strong activation ability of these rationally designed catalysts provides a general solution to the intrinsic limitations of chalcogen bonding catalysis.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Name: 6-Bromo-3-methyl-1H-indole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 6-Bromo-3-methyl-1H-indole, is researched, Molecular C9H8BrN, CAS is 1219741-50-0, about A three-component iodine-catalyzed oxidative coupling reaction: a heterodifunctionalization of 3-methylindoles. Author is Zhang, Wei; Xiang, Shiqun; Fan, Weibin; Jin, Jiang; Li, Yinghua; Huang, Deguang.

A metal-free method for the synthesis of heterodifunctional indole derivatives was developed through TBHP/KI-mediated oxidative coupling. The reaction constructed C-O and C-C bonds in succession with the help of tert-Bu peroxy radicals generated by the TBHP/KI catalytic system, enabling the direct realization of the heterodifunctionalization of indole in one pot. The product of this reaction was a novel heterodifunctional compound This work might provided a new effective method for the synthesis of polycyclic indole compounds

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary

Jeankumar, Variam Ullas; Reshma, Rudraraju Srilakshmi; Vats, Rahul; Janupally, Renuka; Saxena, Shalini; Yogeeswari, Perumal; Sriram, Dharmarajan published the article 《Engineering another class of anti-tubercular lead: Hit to lead optimization of an intriguing class of gyrase ATPase inhibitors》. Keywords: gyrase ATPase inhibitor tuberculosis screening structure; DNA gyrase; Differential scanning fluorimetry; Medium throughput virtual screening; Mycobacterium tuberculosis.They researched the compound: 7-Chloro-4-(piperazin-1-yl)quinoline( cas:837-52-5 ).Safety of 7-Chloro-4-(piperazin-1-yl)quinoline. 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:837-52-5) here.

A structure based medium throughput virtual screening campaign of BITS-Pilani in house chem. library to identify novel binders of Mycobacterium tuberculosis gyrase ATPase domain led to the discovery of a quinoline scaffold. Further medicinal chem. explorations on the right hand core of the early hit, engendered a potent lead demonstrating superior efficacy both in the enzyme and whole cell screening assay. The binding affinity shown at the enzyme level was further corroborated by biophys. characterization techniques. Early pharmacokinetic evaluation of the optimized analog was encouraging and provides interesting potential for further optimization.

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Reference:
Bromide – Wikipedia,
bromide – Wiktionary