Month: October 2022

Application In Synthesis of Trimethylsulfoxonium iodideIn 2020 ,《Regioselective Bronsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N’-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2-a]quinazolin-5(1H)ones》 appeared in Journal of Organic Chemistry. The author of the article were Singh, Priyanka; Kaur, Navpreet; Banerjee, Prabal. The article conveys some information:

A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N’-aryl anthranil hydrazides in the presence of p-toluenesulfonic acid (PTSA). The transformation involves domino imine formation and intramol. cyclization to form 2-arylcyclopropyl-2,3-dihydroquinazolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis. In the part of experimental materials, we found many familiar compounds, such as Trimethylsulfoxonium iodide(cas: 1774-47-6Application In Synthesis of Trimethylsulfoxonium iodide)

Trimethylsulfoxonium iodide(cas: 1774-47-6) reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.Application In Synthesis of Trimethylsulfoxonium iodide

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

Category: iodides-buliding-blocksIn 2021 ,《Selective Modification for Red-Shifted Excitability: A Small Change in Structure, a Huge Change in Photochemistry》 was published in Chemistry – A European Journal. The article was written by Becker, Yvonne; Roth, Sina; Scheurer, Maximilian; Jakob, Andreas; Gacek, Daniel A.; Walla, Peter J.; Dreuw, Andreas; Wachtveitl, Josef; Heckel, Alexander. The article contains the following contents:

We developed three bathochromic, green-light activatable, photolabile protecting groups based on a nitrodibenzofuran (NDBF) core with D-π-A push-pull structures. Variation of donor substituents (D) at the favored ring position enabled us to observe their impact on the photolysis quantum yields. Comparing our new azetidinyl-NDBF (Az-NDBF) photolabile protecting group with our earlier published DMA-NDBF, we obtained insight into its excitation-specific photochem. While the “”two-photon-only”” cage DMA-NDBF was inert against one-photon excitation (1PE) in the visible spectral range, we were able to efficiently release glutamic acid from azetidinyl-NDBF with irradiation at 420 and 530 nm. Thus, a minimal change (a cyclization adding only one carbon atom) resulted in a drastically changed photochem. behavior, which enables photolysis in the green part of the spectrum. In the experiment, the researchers used many compounds, for example, 3-Iodophenol(cas: 626-02-8Category: iodides-buliding-blocks)

3-Iodophenol(cas: 626-02-8) belongs to organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Category: iodides-buliding-blocksIodo 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.

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

Formula: C7H5IO2In 2022 ,《Synthesis, characterization and anti-microbial screening of novel substituted thiadiazole-5-aminotetrazoles》 was published in Chemistry & Biology Interface. The article was written by Gaikwad, Mahadev; Gorepatil, Amarsinha; Gorepatil, Pratapsinha; Kadam, Vishal; Gaikwad, Shivshankar; Shinde, Vishnu; Ingle, Vilas. The article contains the following contents:

An efficient and green synthesis of substituted thiadiazole-5-aminotetrazoles I [R = Ph, benzyl, cinnamyl, etc.] were prepared in-situ by reaction of cyanogen bromide and sodium azide to generate a cyanogen azide as an intermediate in acetonitrile. The cyclization reaction of cyanogen azide and substituted thiadiazoles containing primary amines in acetonitrile-water solvent media, gave the intermediate 1-substituted 5-aminotetrazoles in good yield. In addition, to further evaluate the role of synthesized mols. for antimicrobial activities, and it’s found that compound I [R = 4-O2NC6H4, 2-IC6H4] showed a good antimicrobial for broad range of bacterial and fungal pathogens. After reading the article, we found that the author used 2-Iodobenzoic acid(cas: 88-67-5Formula: C7H5IO2)

2-Iodobenzoic acid(cas: 88-67-5) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. Formula: C7H5IO2 Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.

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

《Discovery of AMG 925, a FLT3 and CDK4 Dual Kinase Inhibitor with Preferential Affinity for the Activated State of FLT3》 was written by Li, Zhihong; Wang, Xianghong; Eksterowicz, John; Gribble, Michael W.; Alba, Grace Q.; Ayres, Merrill; Carlson, Timothy J.; Chen, Ada; Chen, Xiaoqi; Cho, Robert; Connors, Richard V.; DeGraffenreid, Michael; Deignan, Jeffrey T.; Duquette, Jason; Fan, Pingchen; Fisher, Benjamin; Fu, Jiasheng; Huard, Justin N.; Kaizerman, Jacob; Keegan, Kathleen S.; Li, Cong; Li, Kexue; Li, Yunxiao; Liang, Lingming; Liu, Wen; Lively, Sarah E.; Lo, Mei-Chu; Ma, Ji; McMinn, Dustin L.; Mihalic, Jeffrey T.; Modi, Kriti; Ngo, Rachel; Pattabiraman, Kanaka; Piper, Derek E.; Queva, Christophe; Ragains, Mark L.; Suchomel, Julia; Thibault, Steve; Walker, Nigel; Wang, Xiaodong; Wang, Zhulun; Wanska, Malgorzata; Wehn, Paul M.; Weidner, Margaret F.; Zhang, Alex J.; Zhao, Xiaoning; Kamb, Alexander; Wickramasinghe, Dineli; Dai, Kang; McGee, Lawrence R.; Medina, Julio C.. Recommanded Product: 3-Bromo-2-fluoro-4-iodopyridine And the article was included in Journal of Medicinal Chemistry on April 24 ,2014. The article conveys some information:

The authors describe the structural optimization of a lead compound that exhibits dual inhibitory activities against FLT3 and CDK4. A series of pyrido[4′,3′:4,5]pyrrolo[2,3-d]pyrimidine derivatives was synthesized, and SAR anal., using cell-based assays, led to the discovery of AMG 925 (I), a potent and orally bioavailable dual inhibitor of CDK4 and FLT3, including many FLT3 mutants reported to date. Compound I inhibits the proliferation of a panel of human tumor cell lines including Colo205 (Rb+) and U937 (FLT3WT) and induced cell death in MOLM13 (FLT3ITD) and even in MOLM13 (FLT3ITD, D835Y), which exhibits resistance to a number of FLT3 inhibitors currently under clin. development. At well-tolerated doses, compound I leads to significant growth inhibition of MOLM13 xenografts in nude mice, and the activity correlates with inhibition of STAT5 and Rb phosphorylation.3-Bromo-2-fluoro-4-iodopyridine(cas: 884494-52-4Recommanded Product: 3-Bromo-2-fluoro-4-iodopyridine) was used in this study.

3-Bromo-2-fluoro-4-iodopyridine(cas: 884494-52-4) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Recommanded Product: 3-Bromo-2-fluoro-4-iodopyridine

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

《Pd-Cu-mediated synthesis of 2-substituted imidazo[1,2-α]pyridines in water》 was published in Synthetic Communications in 2009. These research results belong to Bakherad, Mohammad; Keivanloo, Ali; Hashemi, Mahdieh. Recommanded Product: 1-Chloro-4-iodo-2-nitrobenzene The article mentions the following:

The reaction of 2-amino-1-(2-propynyl)pyridinium bromide with various iodobenzenes, catalyzed by Pd-Cu, in the presence of sodium lauryl sulfate as the surfactant and cesium carbonate as the base, in water, led to the formation of 2-substituted imidazo[1,2-α]pyridines. After reading the article, we found that the author used 1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3Recommanded Product: 1-Chloro-4-iodo-2-nitrobenzene)

1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3) belongs to organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source of iodine. 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.Recommanded Product: 1-Chloro-4-iodo-2-nitrobenzene

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

Product Details of 161489-05-0On March 10, 1995, Boucher, Eric; Simard, Michel; Wuest, James D. published an article in Journal of Organic Chemistry. The article was 《Use of Hydrogen Bonds to Control Molecular Aggregation. Behavior of Dipyridones and Pyridone-Pyrimidones Designed To Form Cyclic Triplexes》. The article mentions the following:

The tendency of 2-pyridones and related heterocycles to form cyclic hydrogen-bonded dimers allows them to be used as sticky sites that induce mols. in which they are incorporated to associate in particular ways. I, which is constructed from pyridone and pyrimidone subunits linked to a rigid linear acetylenic spacer, incorporates an array of hydrogen-bonding sites designed to favor the formation of a cyclic triplex. I was prepared and the structure of its DMSO solvate was determined by X-ray crystallog. Aggregation does not produce a cyclic triplex but rather gives chains in which adjacent mols. of I are linked by single hydrogen bonds. After reading the article, we found that the author used 4-Iodo-6-methoxypyrimidine(cas: 161489-05-0Product Details of 161489-05-0)

4-Iodo-6-methoxypyrimidine(cas: 161489-05-0) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Product Details of 161489-05-0

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

Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthaleneOn November 15, 2013 ,《Enantioselective Organocatalytic Iodination-Initiated Wagner-Meerwein Rearrangement》 appeared in Organic Letters. The author of the article were Romanov-Michailidis, Fedor; Guenee, Laure; Alexakis, Alexandre. The article conveys some information:

The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent and the lipophilic phosphoric acid act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcs. to β-iodo spiroketones in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement. In addition to this study using (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene, there are many other studies that have used (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene) was used in this study.

(R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene(cas: 189518-78-3) belongs to organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine.Application In Synthesis of (R)-3,3′-Diiodo-2,2′-bis(methoxymethoxy)-1,1′-binaphthalene

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

The author of 《Synthesis of 6-benzylimidazo[2,1-b][1,3]thiazole during Sonogashira coupling》 were Bakherad, Mohammad; Keivanloo, Ali; Tajbakhsh, Mahmood; Kamali, Taghi A.. And the article was published in Synthetic Communications in 2010. SDS of cas: 41252-95-3 The author mentioned the following in the article:

The reaction of 2-amino-3-(2-propynyl)-1,3-thiazolium bromide with various iodobenzenes in the presence of palladium catalyst led to the formation of 6-benzylimidazo[2,1-b][1,3]thiazoles.1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3SDS of cas: 41252-95-3) was used in this study.

1-Chloro-4-iodo-2-nitrobenzene(cas: 41252-95-3) belongs to organic iodides. 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.SDS of cas: 41252-95-3Halogenation of aromatic hydrocarbons is a very important reaction via an electrophilic aromatic substitution.

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

The author of 《Synthesis of new heterocyclic basic derivatives of expected amebicidal activity》 were Abu-Zeid, Y. M.; Abu-Elela, Z.; Ghoneim, K. M.. And the article was published in J. Pharm. Sci. U. Arab. Rep. in 1965. SDS of cas: 3993-79-1 The author mentioned the following in the article:

Halogenated derivatives of the heterocyclic nuclei pyridine, quinoline (I), and pyrimidine (II) were prepared Sulfonation of 8-Cl-I with 6 parts 20% fuming H2SO4 gave the 5-sulfonic acid (III). All trials to brominate or iodinate III and its Na salt or Me ester failed: non-aqueous media, different temperatures with variable duration, and 48% HBr with Br in CH3COOH. Also sulfonation of 5-Br-8-Cl-I was not successful. The II derivatives prepared were: 2-NH2-4-OH-II, 2-NH2-4-Cl-II, 2-NH2-4-OH-II-5-sulfonic acid, and the 2 new compounds 2-NH2-5-iodo-4-OH-II (IV), and 2-NH2-4-Cl-5-iodo II (V). IV was prepared by refluxing mercuric acetate, isocytosine (modified method of Roblin, et al., CA 36, 25329), and iodine in dioxane at 70° for 2 hrs. The precipitate resulting on addition to 15% KI solution was washed and crystallized from CH3COOH; yield 89.6%. V was prepared by refluxing gently POCl3, dimethylaniline, and 5-iodoisocytosine for 3 hrs. On alkalinization with NH4OH, boiling, filtration, and concentration V separated on cooling; yield 48%. In addition to this study using 2-Amino-5-iodopyrimidin-4(1H)-one, there are many other studies that have used 2-Amino-5-iodopyrimidin-4(1H)-one(cas: 3993-79-1SDS of cas: 3993-79-1) was used in this study.

2-Amino-5-iodopyrimidin-4(1H)-one(cas: 3993-79-1) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.SDS of cas: 3993-79-1

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

In 2019,European Journal of Organic Chemistry included an article by Luo, Yi; Guo, Lingmei; Yu, Xinling; Ding, Haosheng; Wang, Huijing; Wu, Yong. Application of 1774-47-6. The article was titled 《Cp*IrIII-Catalyzed [3+2] Annulations of N-Aryl-2-aminopyrimidines with Sulfoxonium Ylides to Access 2-Alkyl Indoles Through C-H Bond Activation》. The information in the text is summarized as follows:

The iridium-catalyzed aromatic C-H alkylation followed by intramol. annulation reactions between N-aryl-2-aminopyridines and sulfoxonium ylides for the synthesis of 2-alkyl indoles is described. This highly efficient and step-economical cyclization reaction displays excellent functional group compatibility and regioselectivity. Afterwards, the directing group in C-H alkylation can be readily removed to obtain the free N-H indoles. Thus, the sulfoxonium ylide, a carbene precursor, is proved as a useful surrogate of diazo compounds in C-H activation chem. In the part of experimental materials, we found many familiar compounds, such as Trimethylsulfoxonium iodide(cas: 1774-47-6Application of 1774-47-6)

Trimethylsulfoxonium iodide(cas: 1774-47-6) reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides.Application of 1774-47-6

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