Category: indole-building-block

Tandem Suzuki-Miyaura cross-coupling/dehydrobromination of 1,1-dibromoalkenes to alkynes with a cyclobutene-1,2-diylbis(imidazolium) salt as catalyst precursor was written by Rahimi, Alireza;Schmidt, Andreas. And the article was included in Synthesis in 2010.SDS of cas: 827-01-0 This article mentions the following:

A cyclobutene-1,2-bis(imidazolium) salt proved to be an efficient catalyst precursor for 1-pot tandem Suzuki-Miyaura/dehydrobromination reactions for the synthesis of alkynes starting from 1,1-dibromo alkenes and Pd(OAc)₂, arylboronates, and KOCMe₃ in PhMe. Starting materials were prepared from aldehydes under Corey-Fuchs conditions. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.SDS of cas: 827-01-0

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

Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate was written by Mizoguchi, Haruki;Seriu, Masaya;Sakakura, Akira. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Product Details of 14204-27-4 This article mentions the following:

A procedure converting tribromocyclopropane to densely functionalized 尾-selenocyclopropylboronic ester using the 1,2-metalate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metalate rearrangement suggested that the reaction proceeds through a seleniranium intermediate. 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, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Product Details of 14204-27-4

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

Rhodium(II)-catalyzed intermolecular [3 + 2] annulation of N-vinyl indoles with N-tosyl-1,2,3-triazoles via an aza-vinyl Rh carbene was written by Jiang, Bo;Shi, Min. And the article was included in Organic Chemistry Frontiers in 2017.Product Details of 4769-96-4 This article mentions the following:

The rhodium(II)-catalyzed annulations of N-vinyl indole derivatives and N-tosyl-1,2,3-triazoles have been developed in this paper, providing a convenient, efficient and straightforward access to synthesize indoles containing a N-dihydropyrrole in moderate to good yields. Furthermore, the reaction of N-vinyl indoles with 2.5 equivalent of N-tosyl-1,2,3-triazoles gave C3-functionalized indoles containing a N-dihydropyrrole in moderate yields after reduction with NaBH₃CN in a one-pot manner. This finding gives a new synthetic protocol for the preparation of indoles containing a N-dihydropyrrole under mild conditions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Product Details of 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. 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 4769-96-4

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

DMSO/t-BuONa/O₂-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles was written by Yang, Ruchun;Yue, Shusheng;Tan, Wei;Xie, Yongfa;Cai, Hu. And the article was included in Journal of Organic Chemistry in 2020.Formula: C8H6N2O2 This article mentions the following:

Aromatic N-heterocycles such as quinolines I [R¹ = H, 8-Cl, 6-OMe, etc.; R² = H, 3-Me, 4-Ph, etc. X = N; Y = CH₂], isoquinolines I [R¹ = H; R² = H, 1-Ph; X = CH₂; Y = N] and indoles II [R¹ = H, 5-F, 4-Br, etc.; R² = H, 2-Me; Y = CH₂, N] were synthesized via a sodium tert-butoxide promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution This reaction proceeded under mild reaction conditions with a good functional group tolerance. Mechanistic studies suggested a radical pathway involved hydrogen abstraction of dimsyl radicals from the N-H bond or 伪-C-H of the substrates, and subsequent oxidation of the nitrogen or 伪-aminoalkyl radicals. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) 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.Formula: C8H6N2O2

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

Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates was written by Lai, Huifang;Xu, Jiexin;Lin, Jin;Su, Biling;Zha, Daijun. And the article was included in Organic Chemistry Frontiers in 2022.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The Ritter-type reaction, without relying on a pre-installed functional group, is a highly efficient tool for the construction of amides. However, the intrinsic chemo-selectivity that determines the generation of amides or byproducts limits the efficiency and yield of the reaction. From 68 different types of hydrates studied, a coordinatively unsaturated inorganic salt hydrate, MgSO₄路2H₂O, controlled chemo-selectivity and eliminated the shortcomings of other synthesis approaches. To rationalize the differences in selectivity of inorganic salt hydrates, their corresponding water content, alkalinity, anions and cations were analyzed. MgSO₄路2H₂O was used with diverse scaffolds and C-H oxygenations, which demonstrated its generality in synthetic utility. Because it is readily available and it significantly improves yield, MgSO₄路2H₂O will have broad application for Ritter-type reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. 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 2-Phenylisoindolin-1-one

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

Convenient synthesis of tricyclic N(1)-C(2)-fused oxazino-indolones via [Au(I)] catalyzed hydrocarboxylation of allenes was written by Pedrazzani, Riccardo;Pinosa, Emanuele;Bertuzzi, Giulio;Monari, Magda;Lauzon, Samuel;Ollevier, Thierry;Bandini, Marco. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.HPLC of Formula: 167631-84-7 This article mentions the following:

A new [Au(I)] catalyzed intramol. hydrocarboxylation of allenes was presented as a valuable synthetic route to oxazino[4,3-a]indolones I [R = H, Me, c-hexyl; R¹ = H, 8-Me, 8-F, etc.]. The use of 3,5-(CF₃)2-C₆H₃-ImPyAuSbF₆ as the optimal catalyst (5 mol%) was necessary to guarantee (i) wide tolerance of functional groups, (ii) mild reaction conditions (r.t., 16 h), and (iii) high yields (up to 90%). Preliminary attempts toward an enantioselective version (81 : 19 er) were also documented by means of a new family of chiral C₁-sym. ImPyAuCl complexes. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7HPLC of Formula: 167631-84-7).

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.HPLC of Formula: 167631-84-7

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

A general method for the highly regioselective introduction of substituents into the 3-position of 5-unsubstituted 4-O-alkyl tetronates was written by Paintner, Franz F.;Allmendinger, Lars;Bauschke, Gerd. And the article was included in Synlett in 2005.Related Products of 14204-27-4 This article mentions the following:

A new, general method for the highly regioselective introduction of substituents into the 3-position of 5-unsubstituted 4-O-alkyl tetronates was developed. 3-Lithiated 4-alkoxy-2-triisopropylsilyloxyfurans generated from the corresponding 3-iodo-precursors via halogen-metal exchange serve as key intermediates. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Related Products of 14204-27-4).

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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Related Products of 14204-27-4

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

Synthesis of bis(indolyl)methanes under dry grinding conditions, promoted by a Lewis acid-surfactant-SiO₂-combined nanocatalyst was written by Wu, Zhiqiang;Wang, Gang;Yuan, Shuo;Wu, Dan;Liu, Wanyi;Ma, Baojun;Bi, Shuxian;Zhan, Haijuan;Chen, Xiaoyan. And the article was included in Green Chemistry in 2019.Recommanded Product: 4769-96-4 This article mentions the following:

An in situ developed Lewis acid-surfactant-SiO₂-combined (LASSC) nanocatalyst was used, for the first time, as a green and effective promoting medium for the electrophilic activation of aldehydes RCHO (R = 4-nitrophenyl, 2,4-dichlorophenyl, 3,4-dihydroxyphenyl, etc.) under solvent-free and dry grinding conditions. The advantages of using the LASSC nanocatalyst include avoiding the generation of wastewater containing sodium dodecyl sulfate and the use of toxic reagents, excellent reusability of the catalyst, and obtaining a high yield of bis(indolyl)methanes I (R¹ = 6-NO₂, 2-Me, 3-Me, etc.). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 4769-96-4).

6-Nitro-1H-indole (cas: 4769-96-4) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 4769-96-4

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

Synthesis and evaluation of new isatin derivatives for cytotoxic activity was written by Priyanka, K. Blessi;Manasa, C.;Sammaiah, G.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Computed Properties of C8H4N2O4 This article mentions the following:

A series of semicarbazones I (R = 5-Br, 7-NO₂, 5-CH₃, etc.) was synthesized and screened for their cytotoxic activity by MTT assay method. All synthesized compounds I exhibited significant cytotoxicity in a concentration-dependent manner. The IC₅₀ values of all test compounds I were found to be between 19.27 and 52.45 mM for MCF-7 cell lines and between 14.10 and 31.6 mM for HeLa cell lines. All the synthesized compounds have shown moderate antioxidant activity. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Computed Properties of C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Computed Properties of C8H4N2O4

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