20/02/2023 - Page 4 of 14 - Indole Building Blocks

Wang, Le et al. published their research in Organic Letters in 2020 | CAS: 4583-55-5

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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.Synthetic Route of C10H10BrN

Fe-Catalyzed Sequential C(sp³)-H/N-H Annulation of 2-Methylindoles with Ethyl Trifluoropyruvate at Room Temperature: Construction of Pyrrolo[1,2-婵炵鍋愮€电導ndoles was written by Wang, Le;Zhou, Jia;Chen, Han-Qia;Li, Dong-Li;Lin, Jun-Bing;Li, Ke;Ding, Tong-Mei;Zhang, Shu-Yu. And the article was included in Organic Letters in 2020.Synthetic Route of C10H10BrN This article mentions the following:

An efficient and benign iron-catalyzed room-temperature method was developed for direct sequential C(sp³)-H/N-H annulation to construct pyrroloindole scaffolds. This strategy features cheap and readily available raw materials and mild room-temperature reaction conditions and provides a green and practical method for the one-pot rapid synthesis of a wide range of diversely functionalized pyrrolo[1,2-婵炵鍋愮€电導ndoles. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Synthetic Route of C10H10BrN).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from闂佽壈浜崹淇沜illus thuringiensis闂佽壈浜粋鍧闂佽壈浜崹淇沜illus velezensis闂佽壈浜粋鍧 their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Lei et al. published their research in Angewandte Chemie, International Edition in 2013 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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 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). Recommanded Product: 5-Isopropylindoline-2,3-dione

Palladium-catalyzed oxidative cycloaddition through C-H/N-H activation: access to benzazepines was written by Wang, Lei;Huang, Jiayao;Peng, Shiyong;Liu, Hui;Jiang, Xuefeng;Wang, Jian. And the article was included in Angewandte Chemie, International Edition in 2013.Recommanded Product: 5-Isopropylindoline-2,3-dione This article mentions the following:

A synthesis of benzazepine heterocycles from isatins and alkynes via direct Pd-catalyzed oxidative cycloaddition is developed. Heterocycles are well tolerated in the reaction, which allows access to a number of unique mol. structures. The significance of the benzazepine scaffold as a structural element should render this method attractive for both synthetic and medicinal chem. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Recommanded Product: 5-Isopropylindoline-2,3-dione).

Ding, Zhenhua et al. published their research in Angewandte Chemie, International Edition in 2013 | CAS: 827-01-0

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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 5-Chloroindole-3-carboxaldehyde

Cobalt-Catalyzed Intramolecular Olefin Hydroarylation Leading to Dihydropyrroloindoles and Tetrahydropyridoindoles was written by Ding, Zhenhua;Yoshikai, Naohiko. And the article was included in Angewandte Chemie, International Edition in 2013.Name: 5-Chloroindole-3-carboxaldehyde This article mentions the following:

The authors developed an intramol. olefin hydroarylation reaction using a cobalt nitrogen-heterocyclic carbene (NHC) as a catalyst. The title compounds thus formed included dihydropyrroloindole derivatives and tetrahydropyridoindole derivatives The synthesis of the target compounds was achieved by a directed carbon-hydrogen bond (C-H bond) activation. Cobalt bromide (CoBr₂), 4,5-dihydro-1,3-bis(2,4,6-trimethylphenyl)-1H-imidazolium chloride (SImes chloride) was used as catalyst combination and [(Trimethylsilyl)methyl]magnesium chloride (Grignard reagent) was used as additive. A cyclization of N-[[1-(3-butenyl)-1H-indol-3-yl]methylene]-4-methoxybenzenamine (I) (indole alkene imine Schiff base) gave a pyrrolo[1,2-a]indolecarboxaldehyde derivative (II) and 6,7,8,9-tetrahydropyrido[1,2-a]indole-10-carboxaldehyde (III). In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Name: 5-Chloroindole-3-carboxaldehyde).

Li, Fahui et al. published their research in Angewandte Chemie, International Edition in 2015 | CAS: 146368-07-2

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) 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. 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.SDS of cas: 146368-07-2

A Covalent Approach for Site-Specific RNA Labeling in Mammalian Cells was written by Li, Fahui;Dong, Jianshu;Hu, Xiaosong;Gong, Weimin;Li, Jiasong;Shen, Jing;Tian, Huifang;Wang, Jiangyun. And the article was included in Angewandte Chemie, International Edition in 2015.SDS of cas: 146368-07-2 This article mentions the following:

Advances in RNA research and RNA nanotechnol. depend on the ability to manipulate and probe RNA with high precision through chem. approaches, both in vitro and in mammalian cells. However, covalent RNA labeling methods with scope and versatility comparable to those of current protein labeling strategies are underdeveloped. A method is reported for the site- and sequence-specific covalent labeling of RNAs in mammalian cells by using tRNA^Ile2-agmatidine synthetase (Tias) and click chem. The crystal structure of Tias in complex with an azide-bearing agmatine analog was solved to unravel the structural basis for Tias/substrate recognition. The unique RNA sequence specificity and plastic Tias/substrate recognition enable the site-specific transfer of azide/alkyne groups to an RNA mol. of interest in vitro and in mammalian cells. Subsequent click chem. reactions facilitate the versatile labeling, functionalization, and visualization of target RNA. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2SDS of cas: 146368-07-2).

Denmark, Scott E. et al. published their research in Journal of the American Chemical Society in 2011 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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.Formula: C14H9NO2S

Catalytic Asymmetric Thiofunctionalization of Unactivated Alkenes was written by Denmark, Scott E.;Kornfilt, David J. P.;Vogler, Thomas. And the article was included in Journal of the American Chemical Society in 2011.Formula: C14H9NO2S This article mentions the following:

Catalytic asym. sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans, e.g., I, by closure with pendant hydroxyl or carboxyl groups. Intermol. thiofunctionalizations were also achieved with simple alcs. or carboxylic acids as the nucleophiles. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Na, Young Min et al. published their research in Bulletin of the Korean Chemical Society in 2011 | 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 827-01-0

Synthesis and activity of novel 1-halogenobenzylindole linked triazole derivatives as antifungal agents was written by Na, Young Min. And the article was included in Bulletin of the Korean Chemical Society in 2011.SDS of cas: 827-01-0 This article mentions the following:

A series of 33 substituted indole-conazole compounds with piperizinyl and difluorophenyl moieties and 2 chiral centers, e. g. I, were prepared and tested for antifungal activity. Several products showed significant activity with both I and II exceeded the clin. prevalent antifungal drug fluconazole against C. albicans including a drug resistant strain. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0SDS of cas: 827-01-0).

Moseley, Jonathan D. et al. published their research in Tetrahedron in 2012 | CAS: 827-01-0

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.Product Details of 827-01-0

A mild robust generic protocol for the Suzuki reaction using an air stable catalyst was written by Moseley, Jonathan D.;Murray, Paul M.;Turp, Edward R.;Tyler, Simon N. G.;Burn, Ross T.. And the article was included in Tetrahedron in 2012.Product Details of 827-01-0 This article mentions the following:

A mild but robust procedure was developed as a 1st pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable Pd pre-catalyst at low loading (闂? mol%) in aqueous solvent mixtures at moderate temperature using K₂CO₃ as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding arylboronates to give complete conversion to the product biphenyls in <1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature A further advantage of these mild conditions of moderate temperature, weak base, and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).

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.Product Details of 827-01-0

Li, Shunian et al. published their research in Organic Chemistry Frontiers in 2021 | CAS: 774-47-0

5,6-Difluoroindoline-2,3-dione (cas: 774-47-0) 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. 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). COA of Formula: C8H3F2NO2

Ni-Catalyzed asymmetric hetero-Diels-Alder reactions of conjugated vinyl azides: Synthesis of chiral azido polycycles was written by Li, Shunian;Lu, Haifeng;Xu, Zhenghu;Wei, Fang. And the article was included in Organic Chemistry Frontiers in 2021.COA of Formula: C8H3F2NO2 This article mentions the following:

The authors describe an efficient Ni(II)/Feng ligand-catalyzed asym. hetero-Diels-Alder reaction between conjugated vinyl azides RC(:CH₂)N₃ [R = 1-cyclohexenyl, 1-cyclopentenyl, C₆H₅CH:CH, C₆H₅C(:CH₂)] and carbonyl groups in compounds such as isatins I (R¹ = H, 5,6-F₂, 7-Br, 5-Me, etc.) and R²C(O)C(O)OR³ (R² = H, Ph, 4-MeOC₆H₄, 4-FC₆H₄, 4-MeC₆H₄, R³ = Me, Et). This method provides a platform for the synthesis of complicated chiral azido polycycles II (R⁴ = H, 10,11-F₂, 9-Br, 11-OCF₃, 11-Me, etc.) and III in high yields and excellent enantioselectivities. In the experiment, the researchers used many compounds, for example, 5,6-Difluoroindoline-2,3-dione (cas: 774-47-0COA of Formula: C8H3F2NO2).

Stirling, C. J. M. et al. published their research in Journal of the Chemical Society in 1960 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Reference of 5388-42-1

Intramolecular reactions of amides. II. Cyclization of amides of 闂?bromocarboxylic acids was written by Stirling, C. J. M.. And the article was included in Journal of the Chemical Society in 1960.Reference of 5388-42-1 This article mentions the following:

C₆H₁₁NH₂ (45 g.) in 100 ml. Et₂O added to 缂?bromobutyryl chloride (from 38 g. acid) in 300 ml. Et₂O gave 38 g. 缂?bromo-N-cyclohexylbutyramide (I), m. 60闂? I heated at 100闂?gave 2-cyclohexyliminotetrahydrofuran H Br salt (II), m. 132闂? from which the base (III), b. 134闂?7 mm., n_D²⁰ 1.4945 (methiodide m. 187-8闂?, was obtained. III (2 g.) in 20 ml. 20% aqueous H₂SO₄ 16 hrs. at 100闂?gave 0.5 g. 缂?butyrolactone (IV), b. 97闂?18 mm., n_D²² 1.4350, and 1.0 g. C₆H₁₁NH₂. III (10 g.) with 2 g. LiAlH₄ gave 4.6 g. 4-cyclohexylaminobutanol, b. 153闂?9 mm., n₂₁_D 1.4830, m. 45.6闂? III with PhMgBr gave a product of unknown structure. I (3.5 g.) refluxed 24 hrs. in 10 ml. EtOH and 500 ml. Et₂O added yielded 0.77 g. C₆H₁₁NH₃Br. Evaporation of the filtrate gave 0.34 g. IV after distillation and 2.1 g. N-cyclohexyl-缂備礁澧介幆鍧県oxybutyramide (V), m. 68.5闂? I (5 g.) with 15 g. powd. KOH 3 min. at 100闂?gave 1.2 g. 1-cyclohexyl-2-pyrrolidone, b. 154闂?7 mm., n_D¹⁴ 1.5005. II (3 g.) refluxed 24 hrs. in 10 ml. EtOH gave 0.4 g. IV and 1.85 g. V. 缂?Ethoxybutyryl chloride (from 1.7 g. acid) with C₆H₁₁NH₂ gave 1.5 g. V. 缂?Bromobutyranilide (VI) resisted cyclization. Ethanolysis of 3 g. VI gave 100% IV. VI (7 g.) and 3.1 g. Et₃N refluxed 1 hr. in 25 ml. EtOH gave 3.3 g. 1-phenyl-2-pyrrolidone, b. 188/14 mm., m. 66-8闂? 缂?Bromo-N-butylbutyramide (25 g.) kept. 1.5 hrs. at 125闂?gave 2.4 g. 2-butyliminotetrahydrofuran (VII), b. 92闂?9 mm., n_D¹⁸ 1.4593. Hydrolysis of 0.9 g. VII in 20% H₂SO₄ 24 hrs. at 100闂?gave 0.2 g. IV and BuNH₂ (55 g. p-nitrobenzoyl derivative, m. 100-1闂?. VII (2.9 g.) with 1 g. LiAlH₄ gave 1.1 g. 4-butylaminobutanol, b. 132闂?10 mm., n_D²¹ 1.4508. N-Benzyl-缂?bromobutyramide, m. 58闂? could not be cyclized. 5-Bromo-N-cyclohexylvaleramide (VIII) (12 g.) heated 1 hr. at 100闂?and Et₂O added yielded 7 g. 2-cyclohexyliminotetrahydropyran HBr salt (IX), m. 108-9闂? IX (4.6 g.) in 20 ml. H₂O was added to 100 ml. saturated brine, 200 ml. Et₂O and 20 ml. 10% aqueous KOH added, then the base quickly extracted and distilled to give 1.9 g. 2-cyclohexyliminotetrahydropyran (X), b. 134闂?8 mm., n_D²¹ 1.4980. X (1.6 g.) with 0.5 g. LiAlH₄ gave 0.89 g. 5-cyclohexylaminopentanol, m. 74-5闂? Ethanolysis of 2 g. VIII gave 0.7 g. C₆H₁₁NH₃Br and 0.3 g. 闂?valerolactone (XI), b. 12 mm. IX (0.6 g.) with 10 ml. 20% H₂SO₄ 16 hrs. at 100闂?gave 0.05 g. XI and 98% C₆H₁₁NH₂. 5-Bromovaleranilide (3 g., m. 96-7闂? refluxed 3 hrs. in 10 ml. EtOH gave 1.27 g. PhNH₃Br and 0.5 g. XI. o-Bromomethylbenzoyl bromide (XIII) (23 g.) with 17 g. PhNH₂ in 300 ml. Et₂O gave 15 g. 2-bromomethylbenzanilide (XIII), m. 83闂? XIII fused at 130闂?gave 1,3-dihydro-1-phenyliminoisobenzofuran HBr salt (XIV), m. 164-5闂? XIV (14 g.) in H₂O basified with aqueous Na₂CO₃ gave 10 g. 1,3-dihydro-1-phenyliminoisofuran (XV), m. 99.5闂? XV (0.75 g.) in 20% H₂SO₄ 1.5 hrs. at 100闂?gave 0.40 g. phthalide (XVI) and 92% PhNH₂. XV (1 g.) 2 hrs. at 300闂?gave 0.7 g. N-phenylisoindolinone, m. 166-7闂? XV (3.5 g.) with 1 g. LiAlH₄ gave 2.7 g. 2-hydroxymethyl-N-phenylbenzylamine, b. 156闂?0.03 mm., m. 59-60闂? XII (21 g.) with 18 g. PhCH₂NH₂ in 250 ml. Et₂O gave 7 g. 1-benzylimino-1,3-dihydroisobenzofuran (XVII), m. 37-8闂? n_D²⁵ 1.6103 (methiodide, m. 143-4闂?. Hydrolysis of XVII with 20% H₂SO₄ gave 88% XVI and 97% PhCH₂NH₂. XVII.HBr (5 g.) refluxed 5 hrs. in 10 ml. EtOH gave 1.62 g. PhCH₂NH₃Br, m. 225闂? 1.13 g. XVI, and 0.5 g. N-benzyl-2-ethoxymethylbenzamide, m. 86.5闂? XVI (3 g.) and PhCH₂NH₂ heated 3 hrs. at 260闂?gave 3.2 g. 2-benzylisoindolinone, m. 90闂? Similarly, XVI and C₆H₁₁NH₂ gave 2-cyclohexylisoindolinone, m. 112-13闂? XII (10.5 g.) with 7.2 g. C₆H₁₁NH₂ in 150 ml. Et₂O gave 4 g. 1-cyclohexylimino-1,3-dihydrobenzofuran (XVIII), m. 79-80闂?(methiodide m. 202闂?. Hydrolysis of XVIII gave 92% XVI and 87% C₆H₁₁NH₂. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Tao, Zhonglin et al. published their research in Journal of the American Chemical Society in 2018 | CAS: 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.SDS of cas: 14204-27-4

Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration was written by Tao, Zhonglin;Robb, Kevin A.;Panger, Jesse L.;Denmark, Scott E.. And the article was included in Journal of the American Chemical Society in 2018.SDS of cas: 14204-27-4 This article mentions the following:

A catalytic, enantioselective method for the preparation of chiral, non-racemic, alkylboronic esters bearing two vicinal stereogenic centers is described. The reaction proceeds via a 1,2-migration of a zwitterionic thiiranium-boronate complex to give exclusively anti carbosulfenylation products. A broad scope of aryl groups migrate with good yield and excellent enantioselectivity (up to 99:1 e.r.). Similarly, a range of di- and trisubstituted alkenylboronic esters are competent reaction partners. This method provides access to both secondary and tertiary chiral alkylboronic esters. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4SDS of cas: 14204-27-4).