Month: January 2023

Hypervalent Iodine Reagents Enable C(sp²)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids was written by Pan, Yue;Liu, Zhengyi;Zou, Peng;Chen, Yali;Chen, Yiyun. And the article was included in Organic Letters in 2022.SDS of cas: 4769-96-4 This article mentions the following:

The sulfonamidyl (hetero)arenes synthesis by the C(sp²)-H amidation from bench-stable amidyl-iminophenylacetic acids was reported. The hypervalent iodine reagents covalently activated iminophenylacetic acids for the facile sulfonamidyl radical generation under mild photocatalytic oxidative conditions. Diversified indoles, pyrroles, imidazopyridines and fused arenes underwent the C(sp²)-H amidation with excellent chemoselectivity and regioselectivity. This reaction performed well under neutral aqueous conditions with potential biol. applications. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4SDS of cas: 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 4769-96-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Pd(II)-Catalyzed Asymmetric Oxidative Annulation of N-Alkoxyheteroaryl Amides and 1,3-Dienes was written by Zhang, Tao;Shen, Hong-Cheng;Xu, Jia-Cheng;Fan, Tao;Han, Zhi-Yong;Gong, Liu-Zhu. And the article was included in Organic Letters in 2019.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The first Pd(II)-catalyzed asym. oxidative annulation of N-alkoxyaryl amides and 1,3-dienes is reported, which features particular applicability for quick assembly of different types of chiral heterocycles with high yields and enantioselectivities. A novel chiral pyridine-oxazoline bearing a methoxyl group at the C-5 position and a gem-di-Me group on the oxazoline moiety was found to be crucial for conversion. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Safety of 5-Chloroindole-3-carboxaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode was written by Lombardi, Lorenzo;Bellini, Daniele;Bottoni, Andrea;Calvaresi, Matteo;Monari, Magda;Kovtun, Alessandro;Palermo, Vincenzo;Melucci, Manuela;Bandini, Marco. And the article was included in Chemistry – A European Journal in 2020.Product Details of 4583-55-5 This article mentions the following:

The site-selective allylative and allenylative dearomatization of indoles with alcs. was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt % loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H₂O/CH₃CN, 55 C, 6 h), broad substrate scope (33 examples, yield up to 92%) and excellent site- and stereoselectivity characterize the present methodol. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, exptl. and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Product Details of 4583-55-5).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Product Details of 4583-55-5

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes was written by Denmark, Scott E.;Hartmann, Eduard;Kornfilt, David J. P.;Wang, Hao. And the article was included in Nature Chemistry in 2014.Product Details of 14204-27-4 This article mentions the following:

The stereocontrolled introduction of vicinal heteroat. substituents into organic mols. is one of the most powerful ways of adding value and function. Although many methods exist for the introduction of oxygen- and nitrogen-containing substituents, the number of stereocontrolled methods for the introduction of sulfur-containing substituents pales by comparison. Previous reports from our laboratories have described sulfenofunctionalizations of alkenes that construct carbon-sulfur bonds vicinal to carbon-oxygen, carbon-nitrogen or carbon-carbon bonds with high levels of diastereospecificity and enantioselectivity. This process is enabled by the concept of Lewis-base activation of Lewis acids, which provides activation of Group 16 electrophiles. To provide a foundation for the expansion of substrate scope and improved selectivities, we have undertaken a comprehensive study of the catalytically active species. Insights gleaned from kinetic, crystallog. and computational methods have led to the introduction of a new family of sulfenylating agents that provide significantly enhanced selectivities. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 14204-27-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

A comparative study on cisplatin analogs containing 7-azaindole (7AIH) and its seven halogeno-derivatives: Vibrational spectra, DFT calculations and in vitro antiproliferative activity. Crystal and molecular structure of cis-[PtCl₂(4Br7AIH)₂]·DMF was written by Dysz, Karolina;Szmigiel-Bakalarz, Ksenia;Nentwig, Markus;Oeckler, Oliver;Malik-Gajewska, Magdalena;Turlej, Eliza;Michalska, Danuta;Morzyk-Ociepa, Barbara. And the article was included in Polyhedron in 2019.Safety of 3-Bromo-4-chloro-7-azaindole This article mentions the following:

Eight platinum(II) complexes of the general formula cis-[PtCl₂(L)₂] containing 7-azaindole (L = 7AIH) and its halogeno-derivatives: L = 3-chloro-7-azaindole (3Cl7AIH); 3-bromo-7-azaindole (3Br7AIH); 4-chloro-7-azaindole (4Cl7AIH); 4-bromo-7-azaindole (4Br7AIH); 5-bromo-7-azaindole (5Br7AIH); 3-bromo-4-chloro-7-azaindole (3Br4Cl7AIH) and 5-bromo-3-chloro-7-azaindole (5Br3Cl7AIH) were prepared Two complexes, cis-[PtCl₂(3Br4Cl7AIH)₂] (2) and cis-[PtCl₂(4Br7AIH)₂]·DMF, are reported for the first time. Crystal structure of the latter compound has been determined with x-ray diffraction anal. (space group P4₃, with a = 14.775(2), c = 41.640(8) Å, V = 9090(3) ų and Z = 16). For all of these complexes, formation of the cis isomers in the solid state was confirmed by exptl. vibrational (IR and Raman) spectroscopy combined with DFT calculations A complete assignment of the IR and Raman spectra was made on the basis of the calculated potential energy distribution (PED). Stability of complex (2) in DMSO solution was investigated by FT-IR (ATR) spectroscopy. The in vitro antiproliferative activity of cis-[PtCl₂(3Br4Cl7AIH)₂], cis-[PtCl₂(3Cl7AIH)₂] and cis-[PtCl₂(3Br7AIH)₂] was evaluated on selected human cancer cell lines and towards normal mouse fibroblast cell line (BALB/3T3). All complexes are more toxic than cisplatin against Es-2 (ovarian cancer), LNCaP (prostate adenocarcinoma) and MCF7 (breast cancer). Moreover, complex (2) is significantly more active than the other complexes on A549 (lung carcinoma, IC₅₀ = 3.9 μM). However, the three investigated Pt(II) complexes with 7-azaindoles have revealed higher cytotoxicity against a normal cell line (BALB/3T3), in comparison to cisplatin. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Safety of 3-Bromo-4-chloro-7-azaindole).

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Safety of 3-Bromo-4-chloro-7-azaindole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Rapid One-Pot Access to Unique 3,4-Dihydrothiopyrano[3,4-b]indol-1(9H)-imines via Bi(OTf)₃-Catalysed Tandem Friedel-Crafts Alkylation/Thia-Michael Addition was written by Dethe, Dattatraya H.;Boda, Vijay Kumar;Mandal, Anupam. And the article was included in European Journal of Organic Chemistry in 2018.Name: 4-Bromoindole-3-acetic Acid This article mentions the following:

A highly efficient and atom economical one-pot annulation strategy for tetrahydrothiopyrano[3,4-b]indoles, e.g., I, is presented. This protocol involves a Bi(OTf)₃ catalyzed tandem Friedel-Crafts alkylation and intramol. thia-Michael addition reactions to furnish target mols. in an efficient manner. The method works effectively on substrates with unprotected indoles and also it is successfully employed to make tetrahydrothiepino[3,4-b]indoles. The scaffolds synthesized are diverse and first of the kind. The reaction is practically simple with broad substrate scope and vast functional group compatibility. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Name: 4-Bromoindole-3-acetic Acid).

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 4-Bromoindole-3-acetic Acid

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate was written by Lai, Huifang;Xu, Jiexin;Lin, Jin;Zha, Daijun. And the article was included in Organic & Biomolecular Chemistry in 2021.Category: indole-building-block This article mentions the following:

Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, authors describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Addnl., the reaction mechanism appears to involve a radical and a carbocationic pathway. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Category: indole-building-block).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs was written by Zhang, Jia-wei;Lu, Guo-ping;Cai, Chun. And the article was included in Catalysis Communications in 2016.Computed Properties of C8H6N2O2 This article mentions the following:

Highly dispersed Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with corresponding single-component catalysts; optimal composition of the Ni-Co BMNPs was screened, which proved to be crucial in both the selectivity and yields. Excellent performance of Ni-Co BMNPs can be ascribed to the improved dispersion of active sites on the BMNPs surface (compared with Ni NPs) and the electron transfer from cobalt to nickel. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Computed Properties of C8H6N2O2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Iron(III)-catalyzed tandem annulation of indolyl-substituted p-quinone methides with ynamides for the synthesis of cyclopenta[b]indoles was written by Yu, Ke-Yin;Ge, Xiao-Min;Fan, Yi-Jun;Liu, Xiao-Tao;Yang, Xue;Yang, Yu-Han;Zhao, Xian-He;An, Xian-Tao;Fan, Chun-An. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Name: 1,4-Dimethyl-1H-indole-3-carbaldehyde This article mentions the following:

The unique reactivity of indolyl-substituted p-QMs as a new type of two-carbon synthon has been explored for the first time in a novel iron(III)-catalyzed tandem annulation. This (2+2) annulation/retro-4π electrocyclization/imino-Nazarov cyclization cascade reaction is characterized by an unusual structural reconstruction of indolyl-substituted p-QMs, leading to an expeditious assembly of synthetically important functionalized cyclopenta[b]indoles. In the experiment, the researchers used many compounds, for example, 1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4Name: 1,4-Dimethyl-1H-indole-3-carbaldehyde).

1,4-Dimethyl-1H-indole-3-carbaldehyde (cas: 170489-16-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Name: 1,4-Dimethyl-1H-indole-3-carbaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Rate constants for chalcogen group transfers in bimolecular substitution reactions with primary alkyl radicals was written by Curran, Dennis P.;Martin-Esker, Amanda A.;Ko, Sung Bo;Newcomb, Martin. And the article was included in Journal of Organic Chemistry in 1993.COA of Formula: C14H9NO2S This article mentions the following:

Rate constants for group transfers of the MeS, PhS, PhSe, and PhTe groups from chalcogen-substituted acetate, acetonitrile, malonate, and malononitrile compounds, from N-(phenylthio)phthalimide and from Me₂S₂ and Ph₂S₂ to primary alkyl radicals, have been determined by competition kinetics using PTOC (2-thioxopyridyl) esters as the radical precursors and competing trapping agents. Thio group transfers from malononitrile derivatives are marginally faster than the corresponding group transfer from the sym. disulfide, and the rate constant for PhSe group transfer from PhSeSePh is greater than those from the derivatives studied here. Substituent effects suggest that the chalcogen transfer reactions may be concerted. For three cases in which direct comparisons can be made, the rate constants for reactions of phenylchalcogenides are approx. equal to those for halogen atom transfer when the chalcogen and halide are in the same row of the periodic table and the radical resulting from displacement is the same. The rate constants reported in this work will be useful for the rational design of synthetic schemes based on homolytic group transfer chem. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.COA of Formula: C14H9NO2S

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles