January 2023 - Page 22 of 26 - Indole Building Blocks

Huang, Hong-Ming et al. published their research in Organic Chemistry Frontiers in 2020 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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.COA of Formula: C9H6ClNO

Cu(II)-Catalyzed formal [4+2] cycloaddition between quinone methides (QMs) and electron-poor 3-vinylindoles was written by Huang, Hong-Ming;Wu, Xu-Yan;Leng, Bo-Rong;Zhu, Yi-Long;Meng, Xin-Chao;Hong, Yu;Jiang, Bo;Wang, De-Cai. And the article was included in Organic Chemistry Frontiers in 2020.COA of Formula: C9H6ClNO This article mentions the following:

A new Cu(II)-catalyzed formal [4+2] cycloaddition between o-hydroxybenzyl alcs./quinone methides (QMs) including para-quinone methides (p-QMs) and ortho-quinone methides (o-QMs) and electron-poor 3-vinylindoles was established. A wide range of richly decorated indole-containing chromane derivatives, e.g., I, was synthesized in acceptable yields and diastereoselectivity. Based on several control experiments, a possible mechanism was also proposed to elucidate the catalytic cycle pathway. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0COA of Formula: C9H6ClNO).

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

Sakurai, Buhei et al. published their research in Bulletin of the Chemical Society of Japan in 1930 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Electric Literature of C14H11NO

The electrolytic reduction of phthalimides. I was written by Sakurai, Buhei. And the article was included in Bulletin of the Chemical Society of Japan in 1930.Electric Literature of C14H11NO This article mentions the following:

An alc. HCl solution of phthalimide (I) was electrolyzed between Pb electrodes, at 20 amp./sq. dm. and at 20-30°, yielding hydroxyphthalimidinc, m. 105°, needles. Reisert’s hydroxyphalimidine, m. 171° (cf. C. A. 7,2578), was found to be a polymer containing 2 mols. It was also prepd from alc. H₂SO₄ solution Cu electrodes, being used. With stronger acid, at 60 amp./sq. dm. and at 30-40°, Phthalimidine, m. 149°, needles, was obtained. Phthalimide could not be reduced in 2 N NaOH, but hydrolyzed to phthalamic acid and phthalic acid. Methylphthalimide (II) yielded methylphthalimidine, m. 45°, plates, with Pb cathode; with Cu cathode it yielded methylhydroxyphthalimidine, m. 129°, prisms. In alk. solution II hydrolyzed to phthalic acid and MeNH₂. Ethylphthalimide (III) yielded ethylphthalimidine, colorless oil, with Pb electrodes; with Cu or Ni cathode ethylhydroxyphthalimidine was obtained instead. In alk. solution III hydrolyzed to ethylphthalamic acid, m. 136°, needles, also phthalic acid and EtNH₂. Phenylphthalimide (IV) yielded phenylphthalimidine, scaly crystals. Hydroxyphenylphthalimide could not be obtained. In alk. solution IV hydrolyzed completely into phthalic acid and PhNH₂. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

Wen, Kangmei et al. published their research in ACS Omega in 2022 | CAS: 89245-41-0

4-Bromoindole-3-acetic Acid (cas: 89245-41-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Application In Synthesis of 4-Bromoindole-3-acetic Acid

Copper-Mediated Decarboxylative Coupling of 3-Indoleacetic Acids with Pyrazolones was written by Wen, Kangmei;Wu, Yinrong;Chen, Jiewen;Shi, Jie;Zheng, Mulin;Yao, Xingang;Tang, Xiaodong. And the article was included in ACS Omega in 2022.Application In Synthesis of 4-Bromoindole-3-acetic Acid This article mentions the following:

A copper-mediated decarboxylative coupling reaction of 3-indoleacetic acids with pyrazolones was described. This protocol realized new functionalization of pyrazolones under simple reaction conditions and exhibited high functional group compatibility and broad substrate scope. Notably, the products displayed antiproliferative activity against cancer cells. In the experiment, the researchers used many compounds, for example, 4-Bromoindole-3-acetic Acid (cas: 89245-41-0Application In Synthesis of 4-Bromoindole-3-acetic Acid).

Ordonez, Mario et al. published their research in Synthesis in 2012 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 5388-42-1

An easy approach for the synthesis of N-substituted isoindolin-1-ones was written by Ordonez, Mario;Tibhe, Gaurao D.;Zamudio-Medina, Angel;Viveros-Ceballos, Jose Luis. And the article was included in Synthesis in 2012.Recommanded Product: 5388-42-1 This article mentions the following:

A practical and efficient two-step synthesis of N-substituted isoindolin-1-ones was developed. The one-pot reaction of 2-formylbenzoic acid with amines and di-Me phosphite proceeds in short time either with conventional heating or microwave irradiation under catalyst-free conditions to afford the corresponding N-substituted di-Me 3-oxoisoindolin-1-ylphosphonates in good yield which, by means of a dephosphonylation reaction with lithium aluminum hydride, give the target N-substituted isoindolin-1-ones in moderate to good yield. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Recommanded Product: 5388-42-1).

Audubert, Clement et al. published their research in Organic Letters in 2017 | CAS: 167631-84-7

Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7) 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.Category: indole-building-block

Mild Esterification of Carboxylic Acids via Continuous Flow Diazotization of Amines was written by Audubert, Clement;Lebel, Helene. And the article was included in Organic Letters in 2017.Category: indole-building-block This article mentions the following:

A new continuous flow protocol for the diazotization of methylamine with 1,3-propanedinitrite in THF is reported. The synthesis of Me esters was achieved in high yields from a variety of carboxylic acids in 20 min at 90 °C. Addnl., this protocol was extended to other aryl and alkyl amines, namely secondary amines, to produce various substituted esters in high yield using 2-MeTHF as a solvent. The reaction conditions were compatible with many functional groups, namely nitrogen-containing heterocycles, alkynes, alkenes, alcs., and phenols. Mechanistic investigations reveal that the reaction appears to proceed through a transient diazonium species rather than a diazo intermediate. In the experiment, the researchers used many compounds, for example, Methyl 5-fluoro-1H-indole-2-carboxylate (cas: 167631-84-7Category: indole-building-block).

Li, Chang-Feng et al. published their research in Organic Letters in 2007 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Recommanded Product: 210345-56-5

Enantioselective Organocatalytic Intramolecular Ring-Closing Friedel-Crafts-Type Alkylation of Indoles was written by Li, Chang-Feng;Liu, Hiu;Liao, Jie;Cao, Yi-Ju;Liu, Xiao-Peng;Xiao, Wen-Jing. And the article was included in Organic Letters in 2007.Recommanded Product: 210345-56-5 This article mentions the following:

An enantioselective organocatalytic intramol. ring-closing Friedel-Crafts-type alkylation of indolyl α,β-unsaturated aldehydes has been developed. This powerful new strategy allows enantioselective access to THPIs (tetrahydropyrano[3,4-b]indoles), e.g., I, and THBCs (tetrahydro-β-carbolines), e.g., II, in a straightforward and atom-economical manner. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Recommanded Product: 210345-56-5).

Singh, R. et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 2006 | CAS: 112656-95-8

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

Structural Studies with Antimicrobial and Antifertility Activity of a Monofunctional Bidentate Ligand with its Boron(III), Palladium(II), and Platinum(II) Complexes was written by Singh, R.;Biyala, M.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2006.Reference of 112656-95-8 This article mentions the following:

The reaction of the sulfur donor Schiff base ligand, (7-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (HL, I), with phenyldihydroxyboron in benzene, and palladium(II)chloride and platinum(II) chloride in ethanol, gave the mononuclear tetracoordinated [PhB(OH)L], [PhB(L)₂], [M(HL)₂]Cl₂ and [M(L)₂] complexes. The Schiff base ligand coordinated to the boron atom in 1:1 and 1:2 molar ratios and to the palladium and platinum metals in only 1:2 molar ratios in the presence of an acidic or basic medium. Tentative structural conclusions are drawn for reaction products based upon elemental anal., elec. conductance, and spectral (electronic, IR, ¹H NMR, ¹³C NMR, and ¹¹B NMR) data. The antifertility activity of the ligand and its nonmetal/metal complexes are discussed with a comparative study in an effective manner. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Reference of 112656-95-8).

Liang, Rong-Bin et al. published their research in Organic Chemistry Frontiers in 2022 | CAS: 14204-27-4

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

External oxidant-free and selective thiofunctionalization of alkenes enabled by photoredox-neutral catalysis was written by Liang, Rong-Bin;Zhu, Can-Ming;Song, Pei-Qi;Zhao, Lei-Min;Tong, Qing-Xiao;Zhong, Jian-Ji. And the article was included in Organic Chemistry Frontiers in 2022.COA of Formula: C14H9NO2S This article mentions the following:

A simple photoredox-neutral approach is reported for the three-component thiohydroxylation, thioalkoxylation and thioamination of vinylarenes ArC(R)=CH₂ (Ar = Ph, 3-bromophenyl, 2H-1,3-benzodioxol-5-yl, etc.; R = H, Me, Ph, thien-2-yl, etc.) towards valuable vicinal S,O- and S,N-disubstituted mols. N-Phenyl-sulfenyl phthalimides I (R¹ = Ph, 2-chlorophenyl, naphthalen-2-yl, etc.), a commonly used sulfur electrophile, were demonstrated to act as a thiyl radical precursor and play a crucial role in this reaction. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

Klein, Larry L. et al. published their research in Tetrahedron Letters in 2013 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.Reference of 150560-58-0

Synthesis of substituted isatins was written by Klein, Larry L.;Tufano, Michael D.. And the article was included in Tetrahedron Letters in 2013.Reference of 150560-58-0 This article mentions the following:

Isatins are valuable intermediates for heterocyclic chem. Most of the common methods for their production are less than adequate when the number and lipophilicity of substituents on the targeted isatin are increased. An an alternative method for preparation of isatins, e.g., I, were developed. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Reference of 150560-58-0).

de Stevens, George et al. published their research in Oesterreichische Chemiker-Zeitung in 1962 | CAS: 90271-86-6

5-Bromo-3-cyanoindole (cas: 90271-86-6) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.HPLC of Formula: 90271-86-6

Synthesis of nitrogen-containing heterocyclic compounds was written by de Stevens, George;Dughi, Marylou;Lukaszewski, Halina;Blatter, Herbert. And the article was included in Oesterreichische Chemiker-Zeitung in 1962.HPLC of Formula: 90271-86-6 This article mentions the following:

A new heterocyclic compound, 1,2,4,5-tetrahydro-3-methyl-1,3-benzodiazepine (I, R = H₂), pKa < 2, was synthesized from o-aminophenylacetic acid methylamide (II) and formaldehyde through I (R = O). Condensation of II with BzH in boiling diethylene glycol dimethyl ether produced only 3-benzylideneoxindole; however, a quant. yield of o-MeNHCOCH₂C₆H₄N:CHPh, λ 260 mμ (ε 15.760), and 320 mμ (ε 6450), was obtained by carrying out the condensation at 95°. New tetracyclic indoles were synthesized from 1-carbethoxymethyl-1,2,3,4-tetrahydro-β-carboline (III, R = EtO), which reacted with MeNH₂ to give a good yield of III (R = NHMe) (IV). IV condensed with formaldehyde in boiling ethanol gave 68% 3-methylaza-1,2,3,4,6,7,12,12boctahydro-2-oxoindolo[2,3-a]pyridocoline (V, R = Me). Condensation of IV with appropriate benzaldehyde gave V (R = Ph, p-ClC₆H₄, 3,4,5-(MeO)₃C₆H₂, and p-MeOC₆H₄). Reduction of the cyclic amides with LiAlH₄ resulted in loss of carbonyl group. Reduction of IV with LiAlH₄ gave the corresponding amino alcohol (VI), which with HCHO gave VII. Replacement of formaldehyde with benzaldehyde did not produce the expected oxazine but the dimeric compound (VIII). Condensation of indole-3-carboxaldehyde with nitropropane in presence of (NH₄)₂HPO₄, AcOH, and Ac₂O resulted in 3-cyanoindole, 60%, m. 178°. This method was extended to other aromatic aldehydes to give: 5-bromo-3-cyanoindole, 41%; 3-cyano-7-azaindole, 40%; p-dimethylaminobenzonitrile, 77%; p-chlorobenzonitrile, 50%; 3,4,5-trimethoxybenzonitrile, 74%; p-isopropylbenzonitrile, 30%. 20 references. In the experiment, the researchers used many compounds, for example, 5-Bromo-3-cyanoindole (cas: 90271-86-6HPLC of Formula: 90271-86-6).