10/02/2023 - Page 5 of 13 - Indole Building Blocks

Niemeyer, Zachary L. et al. published their research in Journal of the American Chemical Society 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Formula: C10H8ClNO2

Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization was written by Niemeyer, Zachary L.;Pindi, Suresh;Khrakovsky, Dimitri A.;Kuzniewski, Christian N.;Hong, Cynthia M.;Joyce, Leo A.;Sigman, Matthew S.;Toste, F. Dean. And the article was included in Journal of the American Chemical Society in 2017.Formula: C10H8ClNO2 This article mentions the following:

Computed descriptors for acyclic diaminocarbene ligands are developed in the context of a gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization. Surrogate structures enable the rapid identification of parameters that reveal mechanistic characteristics. The observed selectivity trends are validated in a robust multivariate anal. facilitating the development of a highly enantioselective process. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Formula: C10H8ClNO2).

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

Zhuang, Weihui et al. published their research in Organic Chemistry Frontiers in 2021 | CAS: 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate

Visible-light induced divergent dearomatization of indole derivatives: controlled access to cyclobutane-fused polycycles and 2-substituted indolines was written by Zhuang, Weihui;Cheng, Yuan-Zheng;Huang, Xu-Lun;Huang, Qiufeng;Zhang, Xiao. And the article was included in Organic Chemistry Frontiers in 2021.Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate This article mentions the following:

A photocatalytic protocol for the divergent dearomative functionalization of indole derivatives was reported. Under the irradiation of visible light, either dimerization or reduction occurred selectively by modifying the reaction conditions, leading to the formation of the corresponding cyclobutane-fused polycycles and 2-substituted indolines in good yields with exclusive selectivity. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Recommanded Product: Methyl 5-fluoro-1H-indole-2-carboxylate).

Yang, Ruchun et al. published their research in Journal of Organic Chemistry in 2020 | CAS: 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.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

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).

Jiang, Bo et al. published their research in Organic Chemistry Frontiers in 2017 | CAS: 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

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).

Mizoguchi, Haruki et al. published their research in Chemical Communications (Cambridge, United Kingdom) in 2020 | CAS: 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

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).

Rahimi, Alireza et al. published their research in Synthesis in 2010 | 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

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).

Frysova, Iveta et al. published their research in ARKIVOC (Gainesville, FL, United States) in 2005 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Formula: C8H4N2O4

Polycyclic heterocycles with acidic N-H group. Part VI. The synthesis of some polycyclic heterocyclic compounds related to 3-phenyl-1,2-dihydroquinoxalin-2-one was written by Frysova, Iveta;Slouka, Jan;Gucky, Tomas. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2005.Formula: C8H4N2O4 This article mentions the following:

This work deals with the study of the reactivity of substituted 3-(2-aminophenyl)-1,2-dihydroquinoxalin-2-ones. 3-(2-Amino-4-fluorophenyl)-1,2-dihydroquinoxalin-2-one (I) was prepared by the reaction of 6-fluoro-N-acetylisatin with 1,2-diaminobenzene and further hydrolysis of the acetyl group. The resp. 3-(2-amino-3-nitrophenyl) compound (II) was prepared directly by the reaction of 7-nitroisatin with 1,2-diaminobenzene. Subsequent cyclization of I and II in POCl₃ afforded the corresponding indolo[2,3-b]quinoxalines. Intramol. splitting cyclizations of diazonium salts derived from I and II led to [1]benzofuro[2,3-b]quinoxalines and azo-coupling reactions of the diazonium salts with Et cyanoacetylcarbamate and malonodinitrile gave arylhydrazones. These arylhydrazones were then transformed into 1,3-diaminopyrazoles and 6-azauracils. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Formula: C8H4N2O4).

Ma, Jinhui et al. published their research in Organic Letters in 2021 | 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.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 5-Chloroindole-3-carboxaldehyde

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S₈ and K₂S was written by Ma, Jinhui;Luo, Jiajun;Jiang, Kai;Zhang, Guangwen;Liu, Shubin;Yin, Biaolin. And the article was included in Organic Letters in 2021.Application In Synthesis of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

Herein, a protocol for accessing polycyclic dihydrothiophenes I (R¹ = H, 10-F, 9-Cl, 8-Br, etc.; R² = Ph, 4-FC₆H₄, 3,4-Me₂C₆H₄, etc.; R³ = Et, i-Pr, n-Pr, PhCH₂; R⁴ = H, Me) by means of formal [2+2+1] intramol. dearomatizing cyclization of alkynyl indoles II with K₂S and S₈ as the sources of sulfide is reported. In addition, tetrahydrothienoindolines III (R¹-R³ as above) were stereoselectively synthesized from the corresponding II (R⁴ = H) via a one-pot, two-step protocol involving AgNO₃-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K₂S. 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).

Blessi, Priyanka K. et al. published their research in International Journal of Pharmacy and Pharmaceutical Sciences in 2012 | CAS: 112656-95-8

7-Nitroindoline-2,3-dione (cas: 112656-95-8) 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.Product Details of 112656-95-8

Synthesis and characterization of new indole derivatives for analgesic activity was written by Blessi, Priyanka K.;Maharaj, Pogula;Suresh, S.;Thirupathi, K.;Sammaiah, G.. And the article was included in International Journal of Pharmacy and Pharmaceutical Sciences in 2012.Product Details of 112656-95-8 This article mentions the following:

A series of indole derivatives I(R =H, 7-Cl, 5-Cl, 5-Br, 5-CO₂H, 5-Me, 5-NO₂, 7-NO₂, 7-CO₂Me) were prepared and profiled as antipyretic compounds All the synthesized derivatives were characterized by chromatog., IR, ¹H NMR and MASS spectral anal. The synthesized derivatives were evaluated for in vivo analgesic activity by using Diclofenac sodium as a standard Prepared compound (R = 5-NO₂) showed potent activity when compared to Diclofenac sodium. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Product Details of 112656-95-8).

Mino, Takashi et al. published their research in Organic & Biomolecular Chemistry in 2016 | CAS: 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application of 4769-96-4

Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles was written by Mino, Takashi;Nishikawa, Kenji;Asano, Moeko;Shima, Yamato;Ebisawa, Toshibumi;Yoshida, Yasushi;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2016.Application of 4769-96-4 This article mentions the following:

Such chiral phosphine-internal olefin hybrid type ligands as N-1-adamantyl-N-cinnamylaniline derivatives 1 with C(aryl)-N(amine) bond axial chirality were synthesized and utilized for the palladium-catalyzed asym. allylic alkylation of indoles to afford the desired products in high enantioselectivities (up to 98% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Application of 4769-96-4).