Category: iodides-buliding-blocks

Iron(II)-Catalyzed Heck-Type Coupling of Vinylarenes with Alkyl Iodides was written by Xiong, Haigen;Li, Yajun;Qian, Bo;Wei, Rongbiao;Van der Eycken, Erik V.;Bao, Hongli. And the article was included in Organic Letters in 2019.Category: iodides-buliding-blocks This article mentions the following:

An iron(II)-catalyzed radical alkyl Heck-type reaction of alkyl iodides with vinylarenes under mild conditions has been reported. T-Bu peroxybenzoate (TBPB) behaves simultaneously as a radical relay initiator, a precursor for the generation of alkyl radical from alkyl iodides, and an oxidant to recycle iron(II)/iron(III). Unactivated primary, secondary, and tertiary alkyl iodides are compatible with the reaction conditions. The mechanistic studies suggest that a radical-polar-crossover pathway might be involved in the catalytic cycle. In the experiment, the researchers used many compounds, for example, 1-Chloro-4-iodobutane (cas: 10297-05-9Category: iodides-buliding-blocks).

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. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Category: iodides-buliding-blocks

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

Metal-Free Hypervalent-Iodine-Promoted C3 Difluorination and C2 Oxidation of N-Substituted Indoles was written by Sun, Xin;Zhao, Xiao-Jing;Wu, Bin. And the article was included in Asian Journal of Organic Chemistry in 2017.Computed Properties of C8H7IO4 This article mentions the following:

A metal-free, highly regioselective C3 difluorination and C2 oxidation of N-substituted indoles I (R¹ = 5-Br, 7-Cl, 3,6-F₂, etc.; R² = Bn, 4-ClC₆H₄CH₂, 2,3,5-F₃C₆H₂CH₂, etc.) with the aid of in situ generated PhIF₂ in the presence of two types of fluorinating agents such as Pyr·HF and Et₃N·HF was reported. This reaction provided 3,3-difluoro-2-oxindoles II with yields up to 64% under mild reaction conditions. A mechanism for this reaction was proposed. In the experiment, the researchers used many compounds, for example, Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7Computed Properties of C8H7IO4).

Methyl 3,5-dihydroxy-4-iodobenzoate (cas: 338454-02-7) 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. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.Computed Properties of C8H7IO4

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

Small-Molecule Anticonvulsant Agents with Potent In Vitro Neuroprotection and Favorable Drug-Like Properties was written by Smith, Garry R.;Brenneman, Douglas E.;Zhang, Yan;Du, Yanming;Reitz, Allen B.. And the article was included in Journal of Molecular Neuroscience in 2014.Formula: C6H3F2I This article mentions the following:

Severe seizure activity is associated with reoccurring cycles of excitotoxicity and oxidative stress that result in progressive neuronal damage and death. Intervention with these pathol. processes is a compelling disease-modifying strategy for the treatment of seizure disorders. We have optimized a series of small mols. for neuroprotective and anticonvulsant activity as well as altered their phys. properties to address potential metabolic liabilities, to improve CNS penetration, and to prolong the duration of action in vivo. Utilizing phenotypic screening of hippocampal cultures with nutrient medium depleted of antioxidants as a disease model, cell death and decreased neuronal viability produced by acute treatment with glutamate or hydrogen peroxide were prevented. Modifications to our previously reported proof of concept compounds have resulted in a lead which has full neuroprotective action at <1 nM and antiseizure activity across six animal models including the kindled rat and displays excellent pharmacokinetics including high exposure to the brain. These modifications have also eliminated the requirement for a chiral mol., removing the possibility of racemization and making large-scale synthesis more easily accessible. These studies strengthen our earlier findings which indicate that potent, multifunctional neuroprotective anticonvulsants are feasible within a single mol. entity which also possesses favorable CNS-active drug properties in vitro and in vivo. In the experiment, the researchers used many compounds, for example, 1,2-Difluoro-3-iodobenzene (cas: 64248-57-3Formula: C6H3F2I).

1,2-Difluoro-3-iodobenzene (cas: 64248-57-3) 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. This periodic order also follows the atomic radius of halogens and the length of the carbon-halogen bond.Formula: C6H3F2I

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

Synthesis of 6-substituted 3,4-dihydro-2H-1-benzopyran-2-ones (dihydrocoumarins) via palladium catalyzed coupling reactions was written by Davies, Stephen G.;Pyatt, Dirk;Thomson, Colin. And the article was included in Journal of Organometallic Chemistry in 1990.Synthetic Route of C9H7IO2 This article mentions the following:

6-Alkenyl, 6-alkynyl, and 6-aryl-3,4-dihydrocoumarins have been prepared from 6-bromo-3,4-dihydrocoumarin via palladium-catalyzed coupling reactions. 6-Carbalkoxy- and 6-keto-3,4-dihydrocoumarins have been obtained via palladium-catalyzed carbonylations of 6-bromo- and 6-iodo-3,4-dihydrocoumarins, resp. In the experiment, the researchers used many compounds, for example, 6-Iodochroman-2-one (cas: 128651-99-0Synthetic Route of C9H7IO2).

6-Iodochroman-2-one (cas: 128651-99-0) 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.Synthetic Route of C9H7IO2

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

Electronically unfavorable addition of electron-deficient olefins to isochromenylium tetrafluoroborates initiated by C-1 O-glycosylation was written by Yu, Shu-Yan;Hu, Zhi-Long;Zhang, Hao;Wang, Shaozhong;Yao, Zhu-Jun. And the article was included in Tetrahedron Letters in 2012.Application In Synthesis of 4-Bromo-2-iodophenol This article mentions the following:

Electronically unfavorable reactions between isochromenylium tetrafluoroborates, e.g. I, and electron-deficient olefins have been studied and achieved by assistance of a phenolic hydroxyl group in the olefin substrates, providing the corresponding 2-oxabicyclo[3.3.1]nonane derivatives, e.g. II, diastereoselectively in moderate to satisfactory yields. The new methodol. is initiated by an intermol. C-1 O-glycosylation, and completed with an intramol. Michael addition and an aldol condensation in cascade fashion. 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. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Application In Synthesis of 4-Bromo-2-iodophenol

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

Efficient Copper-Catalyzed Trifluoromethylation of Aromatic and Heteroaromatic Iodides: The Beneficial Anchoring Effect of Borates was written by Gonda, Zsombor;Kovacs, Szabolcs;Weber, Csaba;Gati, Tamas;Meszaros, Attila;Kotschy, Andras;Novak, Zoltan. And the article was included in Organic Letters in 2014.Synthetic Route of C11H14INO This article mentions the following:

Efficient copper-catalyzed trifluoromethylation of aromatic iodides was achieved with TMSCF₃ in the presence of tri-Me borate. The Lewis acid was used to anchor the in situ generated trifluoromethyl anion and suppress its rapid decomposition Broad applicability of the new trifluoromethylating reaction was demonstrated in the functionalization of different aromatic and heteroaromatic iodides. In the experiment, the researchers used many compounds, for example, N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8Synthetic Route of C11H14INO).

N,N-Diethyl-4-iodobenzamide (cas: 77350-52-8) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. 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.Synthetic Route of C11H14INO

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

Ynamide Click chemistry in development of triazole VEGFR2 TK modulators was written by Vojtickova, Margareta;Dobias, Juraj;Hanquet, Gilles;Addova, Gabriela;Cetin-Atalay, Rengul;Yildirim, Deniz Cansen;Bohac, Andrej. And the article was included in European Journal of Medicinal Chemistry in 2015.Recommanded Product: 4-Bromo-2-iodophenol This article mentions the following:

Structure novelty, chem. stability and synthetic feasibility attracted us to design 1,2,3-triazole compounds as potential inhibitors of VEGFR2 tyrosine kinase. Novel triazoles I [R¹ = OH, R² = pyrrrol-3-yl; R¹ = H, OH, R² = 2-pyridinyl; R¹ = H, OH, R² = pyridin-3-yl; R¹ = 1-naphthyl, R² = NHC(:O)NH₂] and II were proposed by oxazole (III from PDB: 1Y6A)/1,2,3-triazole isosteric replacement, mol. modeling and docking. In order to enable synthesis of I and II we developed a methodol. for preparation of ynamide IV [EWG = CO₂Me, Boc, Ts, Ph]. Compound IV was used for all Click chem. reactions leading to triazoles I [R¹ = OH, R² = 3-pyrrolyl, R¹ = 1-naphthyl, R² = NHC(:O)NH₂; R¹ = OH, R² = 2-pyridinyl] and I [R¹ = H, R² = 2-pyridinyl, 3-pyridinyl] . Among the obtained products, I [R¹ = OH, R² = pyrrol-3-yl, pyridin-2-yl; R¹ = H, R² = pyridin-2-yl] specifically bind VEGFR2 TK and modulate its activity by concentration dependent manner. Moreover predicted binding poses of II and II in VEGFR2 TK were similar to the one known for the oxazole inhibitor III (PDB: 1Y6A). Unfortunately the VEGFR2 inhibition by triazoles, e.g., I [R¹ = H, OH, R² = pyridin-2-yl], is lower than that determined for their oxazole bioisosters III and V, resp. Different electronic properties of 1,2,3-triazole/oxazole heterocyclic rings were proposed to be the main reason for the diminished affinity of I [R¹ = OH, R² = pyrrrol-3-yl; R¹ = OH, R² = 2-pyridinyl; R¹ = H R² = pyridin-3-yl; R¹ = 1-naphthyl, R² = NHC(:O)NH₂] to an oxazole III inhibitor binding site in VEGFR2 TK (PDB: 1Y6A or 1Y6B). Moreover I [R¹ = OH, R² = pyrrrol-3-yl; R¹ = H, OH, R² = 2-pyridinyl; R¹ = H R² = pyridin-3-yl; R¹ = 1-naphthyl, R² = NHC(:O)NH₂] were screened on cytotoxic activity against two human hepatocellular carcinoma cell lines. Selective cytotoxic activity of I [R¹ = 1-naphthyl, R² = NHC(:O)NH₂] against aggressive Mahlavu cells has been discovered indicating possible affinity of I [R¹ = 1-naphthyl, R² = NHC(:O)NH₂] to Mahlavu constitutionally active PI3K/Akt pathway. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-iodophenol (cas: 207115-22-8Recommanded Product: 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. 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.Recommanded Product: 4-Bromo-2-iodophenol

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

Coupling of N-heterocycle-fused enyne aldehydes with γ,δ-unsaturated Fischer carbene complexes was written by Zhang, Jianwei;Zhang, Yanshi;Schnatter, Wayne F. K.;Herndon, James W.. And the article was included in Organometallics in 2006.HPLC of Formula: 15813-09-9 This article mentions the following:

The coupling of γ,δ-unsaturated Fischer carbene complexes, e.g. H₂C:CHCH₂CH₂C(OMe):Cr(CO)₅ with enyne aldehyde derivatives fused to indole, imidazole, and pyrazole ring systems, e.g. I (R¹ = Me₃Si, n-Bu; R² = PhCH₂, PhCHMe, ribofuranosyl; R³ = H, Me₃C, Ph), has been examined The reaction leads to heterocycles fused to the hydronaphthalene ring system, e.g. II, in a single step. The products of the reaction feature heterocycles fused either to benzene rings or to a cyclohexane ring. The product distribution correlates with the electronic richness of the heterocyclic ring. A moderate degree of diastereoselectivity was observed using heterocycles featuring chiral nitrogen substituents. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9HPLC of Formula: 15813-09-9).

4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Organoiodine compounds occur widely in organic chemistry, but are relatively rare in nature. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs.HPLC of Formula: 15813-09-9

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

A Practical Chiral Bicyclic Thioglycolate Lactam Auxiliary for Stereoselective Quaternary Carbon Formation was written by Arpin, Azelie;Manthorpe, Jeffrey M.;Gleason, James L.. And the article was included in Organic Letters in 2006.Reference of 10297-05-9 This article mentions the following:

Chiral bicyclic thioglycolate lactams may be prepared in three steps from inexpensive com. materials. The resulting lactams may be alkylated three times, twice using basic enolization and once using reductive enolization, to form α-quaternary carboxylic acid derivatives in high yield and with high diastereoselectivity. The alkylation products may be cleaved under either acidic or reductive conditions to furnish either carboxylic acids or primary alcs., resp. 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 can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Reference of 10297-05-9

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

Construction of peptide macrocycles via palladium-catalyzed multiple S-arylation: An effective strategy to expand the structural diversity of cross-linkers was written by Chu, Xin;Shen, Linhua;Li, Bo;Yang, Peng;Du, Chengzhuo;Wang, Xiaoye;He, Gang;Messaoudi, Samir;Chen, Gong. And the article was included in Organic Letters in 2021.Quality Control of Bis(2-iodothiophen-3-yl)methanone This article mentions the following:

A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions. In the experiment, the researchers used many compounds, for example, Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0Quality Control of Bis(2-iodothiophen-3-yl)methanone).

Bis(2-iodothiophen-3-yl)methanone (cas: 474416-61-0) belongs to iodide derivatives. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. 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.Quality Control of Bis(2-iodothiophen-3-yl)methanone

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