Category: indole-building-block

Introduction of substituents into the benzene ring of indole. IV. Preparation of bromo-, nitro-, and aminoindoles and indolines was written by Terent’ev, A. P.;Preobrazhenskaya, M. N.;Bobkov, A. S.;Sorokina, G. M.. And the article was included in Zhurnal Obshchei Khimii in 1959.SDS of cas: 3484-23-9 This article mentions the following:

To 100 ml. concentrated H₂SO₄ was added dropwise at 5° 11.9 g. indoline, followed by 4.4 ml. HNO₃ (d. 1.5) in 100 ml. concentrated H₂SO₄ added at below 0°; after 1 hr. the mixture was quenched on ice to yield 100% 6-nitroindoline (I), m. 66.5-7.5° (ligroine); refluxing with Ac₂O gave the 1-Ac derivative, m. 154.5-5.0°. Refluxing 6.1 g. I and 9.1 g. chloranil in 300 ml. xylene 5 hrs. gave after treatment with aqueous NaOH 82% 6-nitroindole (II), m. 141-2°. Similarly, 6-nitro-2-methylindoline gave 81% 6-nitro-2-methylindole (III), m. 113.5-14.5°. Heating 1.3 g. II in 100 AcOH with 1.5 g. CrO₃ in 10 ml. H₂O 0.5 hr. on a steam bath gave 45% 6-nitroisatin, decomposing 300°; phenylhydrazone decomposed 265-6°. Similarly, III was oxidized in 1 hr. to 33% 4-nitro-2-acetamidobenzoic acid, m. 225-6°. Nitration of 5-bromo-1-methylindoline with HNO₃-H₂SO₄ at below 0° in 1 hr. gave 100% red 6-nitro-5-bromo-1-methylindoline, m. 73-4°, which heated with chloranil as above gave 54% yellow 6-nitro-5-bromo-1-methylindole, m. 167-8°. Nitration of indoline in Ac₂O with fuming HNO₃ at 10-12° gave a solid acetyl derivative of 5-nitroindoline which refluxed 0.5 hr. with concentrated HCl gave yellow 5-nitroindoline (IV), 74%, m. 91-1.5°, and a little less soluble dinitroindoline, m. 243-4°. Similarly, 2-methylindoline gave 63% 5-nitro-2-methylindoline, m. 78-9°. IV with chloranil as above gave in 10 hrs. 68% 5-nitroindole, m. 135-7°. 5-Nitro-2-methylindoline similarly gave 65% 5-nitro-2-methylindole, m. 171.5-2.5°. Oxidation of 5-nitroindole in AcOH with CrO₃-H₂O 1 hr. gave 5-nitro-2-aminobenzoic acid, decomposing 275.2-6.0°, which refluxed 1 hr. with 50% H₂SO₄ gave p-nitroaniline. To 5.4 g. 5-nitroindole in 50 ml. EtOH was added a little Raney Ni followed by dropwise addition of 100 ml. N₂H₄.H₂O over several hrs. at reflux; the filtered solution gave 82% 5-aminoindole, b₆ 190°, decomposing 129-30°; Bz derivative m. 166-7°. Similar reduction of 5-nitro-2-methylindole gave 76% 5-amino-2-methylindole, m. 156-6.5°; Bz derivative m. 192-2.5°. Similarly, 6-nitro-2-methylindole gave 43% 6-amino-2-methylindole, b₄ 170-7°, m. 84-5°; Bz derivative m. 210°. 6-Nitroindole gave 77% 6-aminoindole, b₁ 138°, m. 67-8°; Ac derivative m. 269-71°. Heating 6-nitro-1-acetylindoline (3.8 g.) with 30 g. SnCl₂ in 20 ml. concentrated HCl 25 min. on a steam bath gave after addition of NaOH 89% 6-amino-1-acetylindoline, m. 179-9.5°. Reduction of 6-nitro-2-methylindoline with N₂H₄ as above gave 91% yellow 6-amino-2-methylindoline, b₁₇ 175-80°, m. 61-2°; HCl salt, decomposed 230-5°. Similarly, 5-nitroindoline gave 97% 5-aminoindoline, m. 678.5°, whose diacetyl derivative, m. 211-12.5°. Similarly was prepared 93% 5-amino-2-methylindoline, b₉ 155-8°, m. 92°. Bromination of 2-methylindoline with Br in AcOH in the presence of H₂SO₄ gave in 1 hr. 63.5% 5-bromo-2-methylindoline (V), b₃ 130-45° (some decomposition) crude, b₃ 132-3.5°, d₂₀ 1.4550, n_D²⁰ 1.6085; Bz derivative m. 157°. Similarly, indoline gave 72.7% 5-bromoindoline, b₂ 114-14.5°, 1.5240, 1.6311; Ac derivative m. 119-19.5°. V and chloranil, as above, gave 54% 5-bromo-2-methylindole, b₄ 155-62° (some decomposition), m. 97-8°; this with formalin and aqueous Me₂NH in AcOH gave 5-bromo-2-methylskatyldimethylamine, m. 145-7°. 5-Bromoindoline and chloranil gave 47% 5-bromoindole, m. 92-3°. Cf. Colo, et al., C.A. 49, 14733a. In the experiment, the researchers used many compounds, for example, 2-Methyl-6-nitro-1H-indole (cas: 3484-23-9SDS of cas: 3484-23-9).

2-Methyl-6-nitro-1H-indole (cas: 3484-23-9) 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. 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: 3484-23-9

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

Chlorinated auxins-how does Arabidopsis Thaliana deal with them was written by Walter, Antje;Caputi, Lorenzo;O’connor, Sarah;Van Pee, Karl-Heinz;Ludwig-Muelle, Jutta. And the article was included in International Journal of Molecular Sciences in 2020.Electric Literature of C10H8ClNO2 This article mentions the following:

Plant hormones have various functions in plants and play crucial roles in all developmental and differentiation stages. Auxins constitute one of the most important groups with the major representative indole-3-acetic acid (IAA). A halogenated derivate of IAA, 4-chloro-indole-3-acetic acid (4-Cl-IAA), has previously been identified in Pisum sativum and other legumes. While the enzymes responsible for the halogenation of compounds in bacteria and fungi are well studied, the metabolic pathways leading to the production of 4-Cl-IAA in plants, especially the halogenating reaction, are still unknown. The type of chlorinated indole derivatives that could be expected was determined by incubating wild type A. thaliana with different Cl-tryptophan derivatives We showed that, in addition to chlorinated IAA, chlorinated IAA conjugates were synthesized. Concomitantly, we found that an auxin conjugate synthetase (GH3.3 protein) from A. thaliana was able to convert chlorinated IAAs to amino acid conjugates in vitro. In addition, we showed that the production of halogenated tryptophan (Trp), indole-3-acetonitrile (IAN) and IAA is possible in transgenic A. thaliana in planta with the help of the bacterial halogenating enzymes. Furthermore, it was investigated if there is an effect (i) of exogenously applied Cl-IAA and Cl-Trp and (ii) of endogenously chlorinated substances on the growth phenotype of the plants. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Electric Literature of C10H8ClNO2).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Electric Literature of C10H8ClNO2

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

Magnetically recyclable Sm₂Co₁₇/Cu catalyst to chemoselectively reduce the 3-nitrostyrene into 3-vinylaniline under room temperature was written by Ma, Zhenhui;Liu, Hu;Yue, Ming. And the article was included in Nano Research in 2019.Electric Literature of C8H6N2O2 This article mentions the following:

Using non-noble metal catalysts to chemoselectively reduce the 3-nitrostyrene into 3-vinylaniline is extremely attractive due to the important applications of aromatic amines. However, the separation and recycle of catalytic particles to sustainably catalyze are still challenging on account of their small size. In this communication, we report a novel magnetically recyclable catalyst of Sm₂Co₁₇/Cu to chemoselectively reduce 3-nitrostyrene into 3-vinylaniline by activating ammonia borane (AB) to yield hydrogen. The Sm₂Co₁₇, composited of 180 nm Sm₂Co₁₇ nanomagnet and 10 nm Cu catalyst nanoparticles, shows a high conversion (98%) and a high selectivity (99%) for 3-nitrostyrene under ultrasonic concussion. More importantly, they are easily collected by self-separation method without any magnetic field. As a consequence, the excellent recyclable feature is acquired even underwent 10 cycles. Our approach provides a green strategy to synthesize magnetically recyclable catalysts. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) 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. 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). Electric Literature 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

BrOsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles using thermally stable trifluoromethylthiolating reagent was written by Ma, Bingqing;Shao, Xinxin;Shen, Qilong. And the article was included in Journal of Fluorine Chemistry in 2015.Name: 6-Nitro-1H-indole This article mentions the following:

A BrOsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles under mild conditions is described. The reaction was insensitive to moisture and oxygen, that should allow for easy handling. In addition, the reaction is compatible with a variety of functional groups. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Name: 6-Nitro-1H-indole).

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.Name: 6-Nitro-1H-indole

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

Functionalization at Nonperipheral Positions of Triazatruxene: Modular Construction of 1,6,11-Triarylated-Triazatruxenes for Potentially Organic Electronics and Optoelectronics was written by Aslan, Murat;Taskesenligil, Yunus;Pravadl, Selin;Saracoglu, Nurullah. And the article was included in Journal of Organic Chemistry in 2022.COA of Formula: C8H6BrNO This article mentions the following:

Functionalization from nonperipheral positions of triazatruxene is representing a challenge. Triarylation of the nonperipheral positions (1, 6, and 11) in triazatruxene scaffold has been achieved for the first time via two approaches. The transformations involve arylation/cyclotrimerization and cyclotrimerization/arylation sequences. POCl3-mediated direct cyclotrimerization of oxindoles containing electron-deficient substituents on the aryl group at the C7-position resulted in the formation of 2-chloroindoles, whereas oxindoles containing electron-donating substituents gave the triazatruxenes. Furthermore, desired triazatruxenes were achieved through cyclotrimerization of 7-bromooxindole followed by coupling with arylboronic acids. As a representative triazatruxene scaffold, the optoelectronic properties of I have also been studied via UV-visible (UV-vis) absorption spectra and fluorescence spectra of I thin films. Also, d. functional theory calculation was realized to get knowledge about frontier MOs. In the light of the information obtained, an organic light-emitting diode (OLED) device utilizing I as an emissive layer was applied to obtain white emission. In brief, this study provides the first examples of the synthesis of triazatruxenes bearing aryl substituents at the nonperipheral positions as candidate compounds for organic electronics, optoelectronics, and material chem. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8COA of Formula: C8H6BrNO).

7-Bromooxindole (cas: 320734-35-8) 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.COA of Formula: C8H6BrNO

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

Cobalt-catalyzed carbonylation of aryl halides was written by Foa, M.;Francalanci, F.;Bencini, E.;Gardano, A.. And the article was included in Journal of Organometallic Chemistry in 1985.Quality Control of 2-Phenylisoindolin-1-one This article mentions the following:

Carbonylation of aromatic and heteroaromatic halides with a catalytic system of alkylcobalt carbonyl complexes, either preformed or made in situ, and bases such as alkoxides, NaOH, and K₂CO₃ in aliphatic alcs produced aromatic esters, acids, lactones, and lactams in high yield and under mild conditions. New anionic cobalt complexes were formed which were characterized by high reactivity toward aromatic halides. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Quality Control of 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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.Quality Control of 2-Phenylisoindolin-1-one

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

Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles was written by Oseka, Maksim;Kimm, Mariliis;Kaabel, Sandra;Jarving, Ivar;Rissanen, Kari;Kanger, Tonis. And the article was included in Organic Letters in 2016.Synthetic Route of C8H4N2O4 This article mentions the following:

A highly enantioselective organocatalytic [2,3]-rearrangement of oxindole derivatives is presented. The reaction was catalyzed by squaramide, and this provides access to 3-hydroxy 3-substituted oxindoles I and II (Ar = Ph, 4-ClC₆H₄, 3-ClC₆H₄, 2-ClC₆H₄, 4-MeOC₆H₄, 4-NO₂C₆H₄, 2-thienyl, 2-naphthyl, etc.; R¹ = H, 5-F, 7-F, 5-MeO, 5-Br, 7-NO₂, etc.; R² = H, Bn, Me, i-Pr, 4-MeC₆H₄CH₂) in high enantiomeric purities. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

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

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

Tandem Reactions via Barton Esters with Intermolecular Addition and Vinyl Radical Substitution onto Indole was written by Coyle, Robert;McArdle, Patrick;Aldabbagh, Fawaz. And the article was included in Journal of Organic Chemistry in 2014.Category: indole-building-block This article mentions the following:

A one-pot initiator-free Barton ester decomposition with tandem radical addition onto alkyl propiolates or phenylacetylene with aromatic substitution of the resultant vinyl radical allows convenient access to new 9-substituted 6,7-dihydropyrido[1,2-a]indoles, e.g., I (X = Me, CHO, CN; R = Me, Et, t-Bu). Pr radical cyclizations compete when forming the expanded 7,8-dihydro-6H-azepino[1,2-a]indole system. 2-Thiopyridinyl S-radical is incorporated into aromatic adducts when using unsubstituted indole-1-alkanoic acid precursors. X-ray crystallog. on substitution products allows selectivity of the radical addition onto less reactive internal alkynes to be determined In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Category: indole-building-block).

3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) 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. 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.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

Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp³)-H Bonds was written by Ma, Dengke;Zhang, Zhihan;Chen, Min;Lin, Zhenyang;Sun, Jianwei. And the article was included in Angewandte Chemie, International Edition in 2019.Computed Properties of C10H10BrN This article mentions the following:

Described here is a direct catalytic asym. functionalization of unactivated alkyl indoles using organocatalysis. In the presence of an effective chiral urea catalyst and a phosphoric acid additive, the intermol. C-C bond formation between alkyl indoles and trifluoropyruvates proceeded with high efficiency and enantiocontrol. Unlike previous asym. C(sp³-H) functionalizations of α-azaarenes, this process does not require the use of either a strong base or an electron-deficient substrate. The excellent enantiocontrol is particularly noteworthy in view of the severe background reaction as well as the complete inability of other types of catalysts evaluated. Control experiments, kinetic studies, and DFT calculations provided important insights into the mechanism. In the experiment, the researchers used many compounds, for example, 5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5Computed Properties of C10H10BrN).

5-Bromo-2,3-dimethyl-1H-indole (cas: 4583-55-5) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C10H10BrN

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

Molecular requirements for auxin activity. I. Halogenated indoles and indoleacetic acid was written by Porter, William L.;Thimann, Kenneth V.. And the article was included in Phytochemistry (Elsevier) in 1965.Related Products of 1912-45-4 This article mentions the following:

2-Chloroindoleacetic acid had 350% of the activity of indoleacetic acid (IAA) in the pea curvature test; the 2-bromo analog had 160% activity and the corresponding Me and Et esters were even more active. In a series of these and other IAA derivatives, the log of the growth activity is a linear function of the NH stretching frequency in the ir spectra and of the Hammett sigma value for the substituent. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Related Products of 1912-45-4).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Related Products of 1912-45-4

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