07/02/2023 - Indole Building Blocks

Molleti, Nagaraju et al. published their research in Organic & Biomolecular Chemistry in 2016 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Quality Control of 5,6-Difluoroindoline-2,3-dione

Catalyst-free synthesis of α¹-oxindole-α-hydroxyphosphonates via phospha-aldol reaction of isatins employing N-heterocyclic phosphine (NHP)-thiourea was written by Molleti, Nagaraju;Yong Kang, Jun. And the article was included in Organic & Biomolecular Chemistry in 2016.Quality Control of 5,6-Difluoroindoline-2,3-dione This article mentions the following:

A highly efficient phospha-aldol reaction for the synthesis of α¹-oxindole-α-hydroxyphosphonates is developed using N-heterocyclic phosphine (NHP)-thiourea as a phosphonylation reagent under catalyst, additive free conditions. This methodol. encompasses a variety of isatin derivatives to provide α¹-oxindole- α-hydroxyphosphonates up to 99% yield. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Quality Control of 5,6-Difluoroindoline-2,3-dione).

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

Barberis, Claude et al. published their research in Tetrahedron Letters in 2005 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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: Methyl 5-fluoro-1H-indole-2-carboxylate

Cu(I)-catalyzed intramolecular cyclization of ene-carbamates: synthesis of indoles and pyrrolo[2,3-c]pyridines was written by Barberis, Claude;Gordon, Thomas D.;Thomas, Christine;Zhang, Xiaolei;Cusack, Kevin P.. And the article was included in Tetrahedron Letters in 2005.Name: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

Over the past few years, the use of palladium-catalyzed aromatic carbon-nitrogen bond forming reactions by the cross-coupling of aryl halides or triflates and amines has become a useful synthetic tool. Herein, a copper(I) catalyst system that allows efficient synthesis of functionalized indoles and pyrrolo[2,3-c]pyridine derivatives was described. This method takes advantage of amino acid promoted copper coupling of amines with aryl halides, in particular, the use of the CuI/L-proline catalyst system. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Name: Methyl 5-fluoro-1H-indole-2-carboxylate).

Chen, Changpeng et al. published their research in Organic Letters in 2017 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 1912-45-4

Iridium-Catalyzed, Weakly Coordination-Assisted Ortho-Alkynylation of (Hetero)aromatic Carboxylic Acids without Cyclization was written by Chen, Changpeng;Liu, Pei;Tang, Jinghua;Deng, Gongda;Zeng, Xiaoming. And the article was included in Organic Letters in 2017.Product Details of 1912-45-4 This article mentions the following:

In the presence of [Cp^*IrCl₂]₂, arylcarboxylic acids and arylacetic acids such as 2-methylbenzoic acid or o-methylphenylacetic acid underwent regioselective directed alkynylation with i-Pr₃SiCCBr mediated by KHCO₃ and air in tert-amyl alc. to yield alkynylbenzoic acids and alkynylphenylacetic acids such as I (X = bond, CH₂) in 32-96% yields. Indolyl- and thienyl carboxylic and acetic acids and benzothiopheneacetic acids also underwent regioselective alkynylation. The reaction mechanism was studied using the alkynylation of potassium 2-methylbenzoate without added KHCO₃, deuterium labeling experiments, and the kinetic isotope effects on alkynylation. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Product Details of 1912-45-4).

Dassonville, Alexandra et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2004 | CAS: 6639-06-1

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Application In Synthesis of 3-(1H-Indol-1-yl)propanoic acid

New N-pyridinyl(methyl)indolalkanamides acting as topical inflammation inhibitors was written by Dassonville, Alexandra;Breteche, Anne;Evano, Johan;Duflos, Muriel;le Baut, Guillaume;Grimaud, Nicole;Petit, Jean-Yves. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Application In Synthesis of 3-(1H-Indol-1-yl)propanoic acid This article mentions the following:

Title compounds were prepared as non-acidic NSAIDs. Pharmacomodulation was carried out at N(1) and C(5) of the indole ring and at the level of the propanamide chain. N-(Pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)indol-3-yl]propanamide represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Application In Synthesis of 3-(1H-Indol-1-yl)propanoic acid).

Mahajan, Y. R. et al. published their research in Science of Synthesis in 2005 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.Category: indole-building-block

Introduction [Synthesis of amides] was written by Mahajan, Y. R.;Weinreb, S. M.. And the article was included in Science of Synthesis in 2005.Category: indole-building-block This article mentions the following:

A review which constitutes an overview of a whole volume which covers the synthesis of compounds containing an amide moiety, including peptides and lactams. These compounds were divided into groups depending on the type of amide and nature of the substituents around the amide functionality. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Category: indole-building-block).

Xiang, Jiachen et al. published their research in Organic & Biomolecular Chemistry in 2015 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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.Safety of 6-Nitro-1H-indole

One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles was written by Xiang, Jiachen;Wang, Jungang;Wang, Miao;Meng, Xianggao;Wu, Anxin. And the article was included in Organic & Biomolecular Chemistry in 2015.Safety of 6-Nitro-1H-indole This article mentions the following:

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM (bis(indolyl)methane) scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).

Lin, Dian-Zhao et al. published their research in Organic Letters in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst was written by Lin, Dian-Zhao;Huang, Jing-Mei. And the article was included in Organic Letters in 2019.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A method for 3-formylation of indoles has been developed through electrochem. decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochem. decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Application In Synthesis of 5-Chloroindole-3-carboxaldehyde).

Nosova, E. V. et al. published their research in Russian Chemical Bulletin in 2011 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 774-47-0

Fluorine-containing quinoline and quinoxaline styryl derivatives: synthesis and photophysical properties was written by Nosova, E. V.;Trashakhova, T. V.;Ustyugov, V. S.;Mochul’skaya, N. N.;Valova, M. S.;Lipunova, G. N.;Charushin, V. N.. And the article was included in Russian Chemical Bulletin in 2011.Recommanded Product: 774-47-0 This article mentions the following:

(E)-2-Styryl-substituted 6,7-difluoroquinolines, e.g., I, and quinoxalines, e.g., II, were synthesized by the condensation of the corresponding 2-methylbenzazines with aromatic aldehydes. Photoluminescence of the synthesized 6,7-difluoro-2-styrylbenzazines was studied. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0Recommanded Product: 774-47-0).

Shao, Fangwei et al. published their research in Dyes and Pigments in 2011 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Category: indole-building-block

Facile synthesis of monofunctional pentamethine carbocyanine fluorophores was written by Shao, Fangwei;Yuan, Hushan;Josephson, Lee;Weissleder, Ralph;Hilderbrand, Scott A.. And the article was included in Dyes and Pigments in 2011.Category: indole-building-block This article mentions the following:

A high-yield route to sym., conjugatable pentamethine carbocyanine dyes with far-red/near IR (NIR) emission between 650 and 700 nm is reported. The dyes are prepared via condensation of indolium or benz[e]indolium inner salts with an alkyl carboxylic acid derivatized malonaldehyde dianil or alternatively in a one-pot reaction without isolation of the malonaldehyde intermediate. The fluorophores are water-soluble, have bright fluorescence emission, are easily prepared in good yield, and are promising candidates for use in a variety of biochem. and in vivo imaging applications. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Category: indole-building-block).

Alexander, Juliana R. et al. published their research in Organic Letters in 2021 | CAS: 3484-23-9

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Safety of 2-Methyl-6-nitro-1H-indole

Silver Mediated Banert Cascade with Carbon Nucleophiles was written by Alexander, Juliana R.;Kevorkian, Paul V.;Topczewski, Joseph J.. And the article was included in Organic Letters in 2021.Safety of 2-Methyl-6-nitro-1H-indole This article mentions the following:

The Banert cascade of propargylic azides was promoted by simple silver salts and the triazafulvene intermediate can be intercepted by carbon nucleophiles. Various indoles (>25 examples, up to 92% yield) and electron-rich heterocycles were effective. The Mayr nucleophilicity parameter (N) was found to correlate to the reaction efficiency, which enabled the formation of Csp³-Csp² and Csp³-Csp³ bonds under otherwise identical conditions from structurally dissimilar nucleophiles. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9Safety of 2-Methyl-6-nitro-1H-indole).