Month: January 2023

Convenient Access to Arylated Spirocyclic Bisphosphonates was written by Lord, Taylor M.;Casino, Stephanie L.;Hartzell, Susan E.;Garcia, Kevin J.;Pike, Robert D.;Stockland, Robert A. Jr.. And the article was included in ChemistrySelect in 2016.Category: iodides-buliding-blocks This article mentions the following:

The synthesis of P-arylated spirocyclic bisphosphonates is described. The title compounds were generated through a process that combined transesterification with a palladium catalyzed P-arylation. The cross-coupling step could be carried out at room temperature using aryl iodides, while analogous reactions involving aryl bromides required heating. Nitrogen, oxygen, and sulfur containing heterocycles were also successfully incorporated into the framework. Using this approach 20 new arylated compounds were generated bearing a range of electrophiles and functional groups. For the more reactive aryl iodides, the catalyst loading could be decreased to 0.3 % Pd per P-H group in scaled-up versions of the method. The two-step process does not require the use of chlorophosphorus reagents. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Category: iodides-buliding-blocks).

3-Iodobenzo[b]thiophene (cas: 36748-88-6) 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. 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.Category: iodides-buliding-blocks

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

Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides was written by Fleuti, Marianne;Bartova, Katerina;Slavetinska, Lenka Postova;Tloust’ova, Eva;Tichy, Michal;Gurska, Sona;Pavlis, Petr;Dzubak, Petr;Hajduch, Marian;Hocek, Michal. And the article was included in Journal of Organic Chemistry in 2020.Related Products of 34091-51-5 This article mentions the following:

A series of 8-substituted 1-methyl-1,4-dihydropyrazolo[3′,4′:4,5]pyrrolo[2,3-d]pyrimidine (methylpyrazolo-fused 7-deazapurine) ribonucleosides has been designed and synthesized. Two synthetic approaches to the key heterocyclic aglycon I, (i) a six-step classical heterocyclization starting from 5-chloro-1-methyl-4-nitropyrazole and (ii) a three-step cross-coupling and cyclization approach starting from the zinc 4,6-dichloropyrimidine, gave comparable total yield of 18% vs. 13%. The glycosylation of I was attempted by three different methods but only the Vorbruggen silyl-base protocol was efficient and stereoselective to give desired β-anomeric nucleoside intermediate. Its nucleophilic substitutions or cross-coupling reactions at position 8 and deprotection of the sugar moiety gave eight derivatives of pyrazolo-fused deazapurine ribonucleosides, e.g. II, some of which were weakly fluorescent. Me, amino and methylsulfanyl derivatives exerted sub-micromolar cytotoxic effects in vitro against a panel of cancer and leukemia cell lines, as well as antiviral effect against hepatitis C virus in the replicon assay. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5Related Products of 34091-51-5).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.Related Products of 34091-51-5

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

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide was written by Boehm, Philip;Roediger, Sven;Bismuto, Alessandro;Morandi, Bill. And the article was included in Angewandte Chemie, International Edition in 2020.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene This article mentions the following:

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined exptl. and computational studies support a reaction mechanism involving in situ generation of CO. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Recommanded Product: 4-Iodo-1,2-dimethoxybenzene).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Recommanded Product: 4-Iodo-1,2-dimethoxybenzene

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

Novel cyanocombretastatins as potent tubulin polymerisation inhibitors was written by Jalily, Pouria H.;Hadfield, John A.;Hirst, Nicholas;Rossington, Steven B.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Electric Literature of C8H7IO2 This article mentions the following:

A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted Ph rings, were synthesized and their antitumor activity was evaluated. The Z-cyanocombretastatins were synthesized in a one-step protocol in high purity and yield. Fluoro, bromo, iodo, and derivatives with boronic acid and an ethyne function at meta position of the B ring were synthesized. In vitro MTT bioassays against human chronic myelogenous leukemia (K562) and transfected breast adenocarcinoma (MDA NQO1) cell lines, revealed promising IC₅₀ inhibitory values in nanomolar range (<50 nM). Introduction of a nitrile function on the olefinic bond not only increased the cytotoxicity of the less active Z-isomers but rendered the analogs as moderate to potent inhibitors of tubulin polymerization comparable to that of CA-4 (IC₅₀ = 2.2 μM). Thus, compound I (IC₅₀ = 6.7 μM) was identified as a lead candidate for a further evaluation. In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Electric Literature of C8H7IO2).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. Organic iodides are widely used in organic synthesis. Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution. 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.Electric Literature of C8H7IO2

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

Palladium and visible-light mediated carbonylative Suzuki-Miyaura coupling of unactivated alkyl halides and aryl boronic acids was written by Roslin, Sara;Odell, Luke R.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Reference of 10297-05-9 This article mentions the following:

Herein, a simple and efficient method for the palladium-catalyzed carbonylation of aryl boronic acids with unactivated alkyl iodides and bromides under visible-light irradiation, ambient temperature and low CO-pressure is presented. Notably, the procedure uses readily available equipment and an inexpensive palladium catalyst to generate the key alkyl radical intermediate. These mild conditions enabled the synthesis of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Reference of 10297-05-9).

1-Chloro-4-iodobutane (cas: 10297-05-9) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. 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.Reference of 10297-05-9

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

Domino Reactions Containing Different Types of Heck Reactions for Selective 3,3- and 1,3-Diarylations of Propenol with Aryl Halides by Triple Catalysis was written by Zhu, Zhi-Qiang;He, Jian-Shi;Wang, Hai-Jun;Huang, Zhi-Zhen. And the article was included in Journal of Organic Chemistry in 2015.Category: iodides-buliding-blocks This article mentions the following:

A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis. In the experiment, the researchers used many compounds, for example, 4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2Category: iodides-buliding-blocks).

4-Iodo-1,2-dimethoxybenzene (cas: 5460-32-2) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. 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.Category: iodides-buliding-blocks

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

Potassium 4-Iodylbenzenesulfonate: Preparation, Structure, and Application as a Reagent for Oxidative Iodination of Arenes was written by Yusubov, Mekhman S.;Yusubova, Roza Y.;Nemykin, Victor N.;Maskaev, Andrey V.;Geraskina, Margarita R.;Kirschning, Andreas;Zhdankin, Viktor V.. And the article was included in European Journal of Organic Chemistry in 2012.Category: iodides-buliding-blocks This article mentions the following:

A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermol. interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60°C for 2 h, followed by filtration of the precipitate In the experiment, the researchers used many compounds, for example, 3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6Category: iodides-buliding-blocks).

3-Iodo-4-methoxybenzaldehyde (cas: 2314-37-6) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Category: iodides-buliding-blocks

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

Iridium-Catalyzed Intramolecular Cycloisomerization between Functionalized Alkyne with Aryl Vinyl Ether: Synthesis of 2-Vinyl-3-functionalized Methylbenzofurans was written by Qiu, Jiawei;Ohno, Shohei;Matsuzaki, Tsuyoshi;Suzuki, Takeyuki;Murai, Kenichi;Arisawa, Mitsuhiro. And the article was included in Journal of Organic Chemistry in 2020.Synthetic Route of C6H4BrIO This article mentions the following:

A cycloisomerization between an aryl vinyl ether and a functionalized alkyne, such as silylalkyne, to give 2,3-disubstituted benzofuran derivatives using [IrCl(cod)]₂, PCy₃, and NaBAr^F₄ has been developed. This catalyst system not only catalyzes the above cycloisomerization but also isomerize a terminal olefin to give an aryl vinyl ether. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Synthetic Route of C6H4BrIO).

4-Bromo-2-iodophenol (cas: 207115-22-8) 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. 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 C6H4BrIO

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

Synthesis and anticancer activities of 5,6,7-trimethoxy-N-phenyl(ethyl)-4-aminoquinazoline derivatives was written by Zhang, Ying;Jin, Linhong;Xiang, Hongmei;Wu, Jian;Wang, Peiyi;Hu, Deyu;Xue, Wei;Yang, Song. And the article was included in European Journal of Medicinal Chemistry in 2013.Formula: C7H6INO2 This article mentions the following:

A series of 5,6,7-trimethoxy-N-phenyl(ethyl)-4-aminoquinazoline compounds was prepared by microwave irradiation and conventional heating methods. Three of these compounds, e.g. I, strongly inhibited extracellular regulated kinase1/2 (ERK1/2) phosphorylation induced by epidermal growth factor (EGF) at 1.28 μM in PC3 cells. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed that all compounds had certain anticancer activities, and the IC₅₀ values of I were 6.2 ± 0.9, 3.2 ± 0.1, and 3.1 ± 0.1 μM against PC3, BGC823, and Bcap37 cells, resp. Acridine orange/ethidium bromide staining, Hoechst 33258 staining, DNA ladder, and flow cytometry analyses revealed that I induced cell apoptosis in PC3 cells, with apoptosis ratios of 11.6% at 1 μM and 31.8% at 10 μM after 72 h. In the experiment, the researchers used many compounds, for example, 2-Amino-4-iodobenzoic acid (cas: 20776-54-9Formula: C7H6INO2).

2-Amino-4-iodobenzoic acid (cas: 20776-54-9) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Formula: C7H6INO2

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

Divergent Strategies for the π-Extension of Heteroaryl Halides Using Norbornadiene as an Acetylene Synthon was written by Jeong, Siyeon;Kim, Eunmin;Kim, Minkyu;Hwang, Ye Ji;Padhi, Birakishore;Choi, Jonghoon;Lee, Yunho;Joo, Jung Min. And the article was included in Organic Letters in 2020.HPLC of Formula: 34091-51-5 This article mentions the following:

Pd-catalyzed multicomponent coupling reactions of five-membered heteroaryl halides and norbornadiene (NBD) were developed. Either direct addition of (benzo)azoles or 2:1 annulation was achieved depending on the propensity of the intermediate complex to undergo palladacycle formation, determined by the nature and substitution pattern of the heteroarene. The obtained exo- and cis-diheteroaryl norbornenes underwent epimerization and retro-Diels-Alder reactions to afford the corresponding trans-isomers and π-extended heteroaromatic systems, resp., demonstrating the versatility of NBD as an acetylene synthon. In the experiment, the researchers used many compounds, for example, 5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5HPLC of Formula: 34091-51-5).

5-Iodo-1-methyl-1H-pyrazole (cas: 34091-51-5) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. 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.HPLC of Formula: 34091-51-5

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