Month: January 2023

Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate was written by Liu, Juyan;Tian, Miaomiao;Li, Ankun;Ji, Liangshuo;Qiu, Di;Zhao, Xia. And the article was included in Tetrahedron Letters in 2021.Related Products of 207115-22-8 This article mentions the following:

A Bronsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF₃-substituted benzofuran derivatives I [R¹ = H, 5-Cl, 6-MeO, etc.; R² = Ph, 2-FC₆H₄, 4-BrC₆H₄, etc.] were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl₃ as the catalyst. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Related Products of 207115-22-8).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Related Products of 207115-22-8

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Design, synthesis, biological evaluation and molecular modelling studies of oxoacetamide warhead containing indole-quinazolinone based novel hybrid analogues as potential pancreatic lipase inhibitors was written by Auti, Prashant S.;Nandi, Arijit;Kumari, Vijeta;Paul, Atish T.. And the article was included in New Journal of Chemistry in 2022.Synthetic Route of C7H6INO2 This article mentions the following:

A novel series of indolyl oxoacetamide-quinazolinone hybrid analogs (9aa-9df) were designed, synthesized, and evaluated for their in vitro pancreatic lipase (PL) inhibitory potential which may lead to efficient anti-obesity agents. All the synthesized hybrid analogs exhibited moderate to potent PL inhibitory activity (IC50 = 32.51 to 4.86 μM). Among all the analogs, 9ak, 9af, 9aj, and 9ah were found to have the most potent PL inhibitory activity (IC50 = 4.86, 5.73, 5.83, and 5.94 μM resp.), as compared to orlistat (IC50 = 0.86 μM). The most potent analogs 9af and 9ak were found to inhibit PL competitively with an inhibition constant (Ki) of 2.136, 1.648 μM. Furthermore, the docking study confirmed the binding of analogs 9ak and 9af (MolDock score of -161.25, -133.67 kcal mol-1) that exhibited docking interactions with important active site amino acids, namely Phe 77, Tyr 114, Ser 152, Arg 256, His 263, etc. Also, the anal. of analog 9ak and 9af in SeeSAR revealed the covalent inhibition of PL. In mol. dynamics simulations of 100 ns, the complex between each analog (9ak & 9af) and PL was found to be stable (RMSD < 1.5 Å). The present work highlights the importance of a hybrid drug design approach for the development of indole and quinazolinone containing hybrids as potential PL inhibitors. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Synthetic Route of C7H6INO2).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Synthetic Route of C7H6INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Visible-Light-Induced Radical Carbo-Cyclization/gem-Diborylation through Triplet Energy Transfer between a Gold Catalyst and Aryl Iodides was written by Zhang, Lumin;Si, Xiaojia;Rominger, Frank;Hashmi, A. Stephen K.. And the article was included in Journal of the American Chemical Society in 2020.Application In Synthesis of 4-Bromo-2-iodophenol This article mentions the following:

Gem-Diboronates I (X = O, S, NBoc; R¹ = H, halo, MeCO, MeO₂C, ^tBu, CF₃, MeSO₂NH; R² = H, Me, Et; R³ = H, Me, ⁱPr, Bu) were prepared by photochem. diboration of propargylic substrates 2-I-R¹C₆H₃XCHR³CCR² with B₂pin₂ catalyzed by gold complex [Au₂(μ-dppm)₂(OTf)₂] with up to 90% yields. Geminal diboronates have attracted significant attention because of their unique structures and reactivity. However, benzofuran-, indole- and benzothiophene-based benzylic gem-diboronates, building blocks for biol. relevant compounds, are unknown. A promising protocol using visible light and aryl iodides for constructing valuable building blocks, including benzofuran-, indole- and benzothiophene-based benzylic gem-diboronates, via radical carbo-cyclization/gem-diborylation of alkynes with a high functional group tolerance is presented. The utility of these gem-diboronates has been demonstrated by a ten gram scale conversion, by versatile transformations, by including the synthesis of approved drug scaffolds and two approved drugs, and even by polymer synthesis. The mechanistic investigation indicates that the merging of the dinuclear gold catalyst (photoexcitation by 315-400 nm UVA light) with Na₂CO₃ is directly responsible for photosensitization of aryl iodides (photoexcitation by 254 nm UV light) with blue LEDs light (410-490 nm, λmax = 465 nm) through an energy transfer (EnT) process, followed by homolytic cleavage of the C-I bond in the aryl iodide substrates. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Application In Synthesis of 4-Bromo-2-iodophenol).

4-Bromo-2-iodophenol (cas: 207115-22-8) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Application In Synthesis of 4-Bromo-2-iodophenol

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reductive Cross-Coupling of α-Oxy Halides Enabled by Thermal Catalysis, Photocatalysis, Electrocatalysis, or Mechanochemistry was written by Zhu, Chen;Lee, Shao-Chi;Chen, Haifeng;Yue, Huifeng;Rueping, Magnus. And the article was included in Angewandte Chemie, International Edition in 2022.Synthetic Route of C8H5IS This article mentions the following:

A reductive cross-coupling reaction of α-oxy halides, simply generated from aldehydes, with a series of C(sp²)- and C(sp)-electrophiles was reported. A wide range of aryl and heteroatom aryl halides, vinyl bromides, alkynyl bromides, and acyl chlorides react with unhindered and hindered aldehyde-derived α-oxy halides by providing protected alcs. as well as α-hydroxy ketones. Noteworthy, the reductive couplings are achieved not only through thermal catalysis with the use of metal reductants but also by photocatalysis, electrochem., and mechanochem. The unrestricted interchange of the four strategies indicates their underlying mechanistic similarities. The generation of NiI intermediate was proposed to be the key point for ketyl radical formation via a single-electron transfer (SET) event, which was rationalized by an array of control experiments and d. functional theory (DFT) calculations In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Synthetic Route of C8H5IS).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Synthetic Route of C8H5IS

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis and antitumor activity of novel pyrimidinyl pyrazole derivatives. III. Synthesis and antitumor activity of 3-phenylpiperazinyl-1-trans-propenes was written by Naito, Hiroyuki;Ohsuki, Satoru;Atsumi, Ryo;Minami, Megumi;Mochizuki, Mineko;Hirotani, Kenji;Kumazawa, Eiji;Ejima, Akio. And the article was included in Chemical & Pharmaceutical Bulletin in 2005.Formula: C6H5FIN This article mentions the following:

A series of 3-[4-phenyl-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propenes, e.g., I, and related compounds were synthesized and evaluated by their cytotoxic activity against several tumor cell lines in vitro and in vivo antitumor activity against some tumor models when administered both i.p. and orally. Compounds with the 3-chloropyridin-2-yl group and the 3-fluoro-5-substituted phenylpiperazinyl group showed significantly potent cytotoxicity by in vitro testing. Among them, the 3-cyano-5-fluorophenyl derivative I exhibited potent antitumor activity against several tumor cells including human carcinoma without causing undesirable effects in mice. In the experiment, the researchers used many compounds, for example, 3-Fluoro-5-iodoaniline (cas: 660-49-1Formula: C6H5FIN).

3-Fluoro-5-iodoaniline (cas: 660-49-1) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Formula: C6H5FIN

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Active Molybdenum-Based Anode for Dehydrogenative Coupling Reactions was written by Beil, Sebastian B.;Mueller, Timo;Sillart, Sydney B.;Franzmann, Peter;Bomm, Alexander;Holtkamp, Michael;Karst, Uwe;Schade, Wolfgang;Waldvogel, Siegfried R.. And the article was included in Angewandte Chemie, International Edition in 2018.Product Details of 5460-32-2 This article mentions the following:

A new and powerful active anode system that can be operated in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) was discovered. In HFIP the Mo anode forms a compact, conductive, and electroactive layer of higher-valent Mo species. This system can replace powerful but stoichiometrically required Mo^V reagents for the dehydrogenative coupling of aryls. This electrolytic reaction is more sustainable and allows the conversion of a broad scope of activated arenes. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Product Details of 5460-32-2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Product Details of 5460-32-2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent was written by Bao, Hanyang;Zhou, Bingwei;Luo, Shu-Ping;Xu, Zheng;Jin, Hongwei;Liu, Yunkui. And the article was included in ACS Catalysis in 2020.Electric Literature of C8H5IS This article mentions the following:

A deoxygenative radical alkylation of aromatic alkynes with alkyl aldehydes for the preparation of allylarenes was successfully achieved. This transformation is accomplished through the reaction of alkyl aldehydes with alkynes in the presence of dipropylamine and Hantzsch ester catalyzed by a P/N heteroleptic Cu(I)-based photosensitizer under photoredox catalysis conditions. Preliminary mechanistic studies reveal that this aldehyde-alkyne coupling process comprises a regioselective radical addition of in-situ-generated alkyl-substituted α-amino radicals to alkynes with subsequent 1,5-proton transfer, C-N bond cleavage and concomitant isomerization of the resulting allyl radical species. Thus, in net result, dipropylamine serves as a traceless linker agent for the deoxygenative radical cross-coupling of alkyl aldehydes with alkynes under photoredox catalysis reaction conditions. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Electric Literature of C8H5IS).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Electric Literature of C8H5IS

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation was written by Romanov-Michailidis, Fedor;Sedillo, Kassandra F.;Neely, Jamie M.;Rovis, Tomislav. And the article was included in Journal of the American Chemical Society in 2015.Related Products of 10297-05-9 This article mentions the following:

α,β-Unsaturated oxime pivalates are proposed to undergo reversible C(sp²)-H insertion with cationic Rh(III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to convert these mols. into piperidines, which are important structural components of numerous pharmaceuticals. Thus, e.g., heterocyclization of unsaturated oxime pivalate I with alkene II in presence of [Rh(MeCN)₃(C₅Me₄CF₃)](SbF₆)₂ afforded dihydropyridine III (99%). In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Related Products of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Related Products of 10297-05-9

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary was written by Chen, Gang;Shigenari, Toshihiko;Jain, Pankaj;Zhang, Zhipeng;Jin, Zhong;He, Jian;Li, Suhua;Mapelli, Claudio;Miller, Michael M.;Poss, Michael A.;Scola, Paul M.;Yeung, Kap-Sun;Yu, Jin-Quan. And the article was included in Journal of the American Chemical Society in 2015.Synthetic Route of C8H9IO2 This article mentions the following:

Palladium-catalyzed β-C-H functionalizations of carboxylic acid derivatives using an auxiliary as a directing group have been extensively explored in the past decade. In comparison to the most widely used auxiliaries in asym. synthesis, the simplicity and practicality of the auxiliaries developed for C-H activation remains to be improved. The authors previously developed a simple N-methoxyamide auxiliary to direct β-C-H activation, albeit this system was not compatible with carboxylic acids containing α-hydrogen atoms. Herein, the authors report the development of a pyridine-type ligand that overcomes this limitation of the N-methoxyamide auxiliary, leading to a significant improvement of β-arylation of carboxylic acid derivatives, especially α-amino acids. The arylation using this practical auxiliary is applied to the gram-scale syntheses of unnatural amino acids, bioactive mols., and chiral bis(oxazoline) ligands. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Synthetic Route of C8H9IO2).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Synthetic Route of C8H9IO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthesis of new bis[heterocycles] by a one-pot Sonogashira coupling reaction was written by Deodhar, Mandar;Black, David StC;Kumar, Naresh. And the article was included in Heterocycles in 2011.Computed Properties of C8H7IO2 This article mentions the following:

Halogenated flavones, isoflavones and indoles were subjected to a one-pot Sonogashira coupling reaction and the synthesis of the target compounds was achieved in good yield. For example, iodination and Sonogashira coupling of Daidzein diacetate [7-(acetyloxy)-3-[4-(acetyloxy)phenyl]-4H-1-benzopyran-4-one] with (trimethylsilyl)acetylene thus provided 2,1-ethynediyl(methoxy-4,1-phenylene)bis[7-methoxy-4H-1-benzopyran-4-one]. The methodol. can be readily adapted to the synthesis of a wide variety of substituted bis[heterocyclic compounds]. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Computed Properties of C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Computed Properties of C8H7IO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com