200-300 | - Page 4 of 43 - Indole Building Blocks

Prey, V. et al. published their research in Monatshefte fuer Chemie in 1960 | 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. 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: 5388-42-1

The rearrangement of 1-thiophthalide was written by Prey, V.;Kerres, B.;Berbalk, H.. And the article was included in Monatshefte fuer Chemie in 1960.SDS of cas: 5388-42-1 This article mentions the following:

The rearrangement of the title compound (I) in the presence of primary, secondary, and tertiary bases, with or without pressure, was studied and a reaction scheme was proposed, and through conductivity, heat of combustion, and infrared measurement, the important intermediate stages for tertiary bases were identified. Thus, 2 g. I and 5 g. PhNH₂ was heated in a sealed tube 3 hrs. at 190闂? and then about 0.1N HCl was added and a brown oil separated; this was crystallized from EtOH and then from H₂O to give 1.65 g. 2-thiophthalide (II), m. 59-60闂? Some similar representative experiments with I were (reagent, molar ratio of reagent to I, temperature, time, product, m. p., % yield given): PhNH₂, 1:5, 180闂? 1 hr., II, 60闂? quant.; PhNH₂, 1:25, 190闂? 2 hrs., N-phenylphthalimide (III), 168闂? 92; PhNH₂, 1:4 (sealed), room, 1 month, I, 116-17闂? 95; PhNH₂, 1:4 (open), room, 1 week, III, 168闂? -; MePhNH, 1:1, 190闂? 3 hrs., I, -, 100; Et₂PhN, 1:5, 190闂? 3 hrs., I, -, 100; o-ClC₆H₄NH₂, 1:5, 190闂? 3 hrs., N-(o-chlorophenyl)phthalimide, 206闂? 86; p-ClC₆H₄NH₂, 1:5, 190闂? 3 hrs., N-(p-chlorophenyl)phthalimide, 182-3闂? 96; o-toluidine, 1:5,190闂? 3 hrs., I,-, 100; BuNH₂, 1:4, 190闂? 3 hrs., o,o’-bis(butylaminomethyl)benzoyl sulfide (IV), 181-2闂? about 5; aqueous NH₃, -, 190闂? 3 hrs., diphthalyldiimide (V), 300闂? -; aqueous NH₃, -, 240闂? 3 hrs., II, -, 40; aqueous NH₃, -, reflux, 3 hrs., phthalide, 68-70闂? 50; pyridine, 1:5, about 100闂? 3 hrs., II,-, 100; quinoline, 1:5, 190闂? 3 hrs., II,-, 100; Et₃N, 1:1, 190闂? 4 hrs., II,-, 97. IV when heated with H₂O gave H₂S, and the filtrate from IV when treated with concentrated HCl gave II. A solution of 2.4 g. NaHS and 5 g. phthalide was heated 3 hrs. at 200闂?and treated with concentrated HCl to give 3.5 g. dibenzyl sulfide-o,o’ dicarboxylic acid, m. 230-3闂? dibutylamide m. 244-6闂? The EtOH filtrate from V was concentrated and the residue was purified with tetrahydrofuran and C to give 21.7% II, m. 54-9闂? In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

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

Avramenko, V. G. et al. published their research in Khimiya Geterotsiklicheskikh Soedinenii in 1974 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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: C10H8ClNO2

Indole derivatives. XCIX. Reaction of indoles with chloroacetic acids was written by Avramenko, V. G.;Nazina, V. D.;Levinova, N. N.;Plutitskii, D. N.;Suvorov, N. N.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1974.Formula: C10H8ClNO2 This article mentions the following:

The indoles I (R = H, Me, Ph; R1 = H, Cl, MeO, HO) were condensed with ClCH2CO2H in aqueous KOH at 240-50闂?and 5 atm to give the indoleacetates II. Similarly, Cl2CHCO2H and HOCH2CO2Et reacted with 1H-indole (III) to give II (R = R1 = H) in 91.5% and 46.3% yield, resp. Condensation of III with PhCH2Cl gave 21% 3-benzyl-1H-indole. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Formula: C10H8ClNO2).

Kim, Ji Hye et al. published their research in Angewandte Chemie, International Edition in 2020 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Formula: C14H9NO2S

Divergent Strain-Release Amino-Functionalization of [1.1.1]Propellane with Electrophilic Nitrogen-Radicals was written by Kim, Ji Hye;Ruffoni, Alessandro;Al-Faiyz, Yasair S. S.;Sheikh, Nadeem S.;Leonori, Daniele. And the article was included in Angewandte Chemie, International Edition in 2020.Formula: C14H9NO2S This article mentions the following:

Herein the authors report the development of a photocatalytic strategy for the divergent preparation of functionalized bicyclo[1.1.1]pentylamines. This approach exploits, for the first time, the ability of nitrogen-radicals to undergo strain-release reaction with [1.1.1]propellane. This reactivity is facilitated by the electrophilic nature of these open-shell intermediates and the presence of strong polar effects in the transition-state for C-N bond formation/ring-opening. With the aid of a simple reductive quenching photoredox cycle, the authors have successfully harnessed this novel radical strain-release amination as part of a multicomponent cascade compatible with several external trapping agents. Overall, this radical strategy enables the rapid construction of novel amino-functionalized building blocks with potential application in medicinal chem. programs as p-substituted aniline bioisosteres. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Formula: C14H9NO2S).

Surya Prakash Rao, H. et al. published their research in Synthetic Communications in 2022 | 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.HPLC of Formula: 5388-42-1

Palladium-catalyzed intramolecular C-N coupling: Facile synthesis of tetracyclic C(3)-aminoisoindolinones was written by Surya Prakash Rao, H.;Prabhakaran, J.. And the article was included in Synthetic Communications in 2022.HPLC of Formula: 5388-42-1 This article mentions the following:

Herein, a new methodol. to access tetracyclic heterocyclic compounds incorporating fused isoindolinone and benzimidazoline or isoindolinone and quinazoline motifs was reported. The palladium-(II) catalyzed intramol. Buchwald-Hartwig C-N coupling involving the C(3) amino and the N(2) 2-bromophenyl groups provided coveted heterocycles in excellent yields. The methodol. was versatile, highly efficient and has a wide scope for the synthesis of a range of medicinally important tetracyclic C(3)-aminoisoindolinones. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1HPLC of Formula: 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.HPLC of Formula: 5388-42-1

Carrillo, Adela I. et al. published their research in Reaction Chemistry & Engineering in 2018 | CAS: 5388-42-1

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

A versatile, immobilized gold catalyst for the reductive amination of aldehydes in batch and flow was written by Carrillo, Adela I.;Llanes, Patricia;Pericas, Miquel A.. And the article was included in Reaction Chemistry & Engineering in 2018.SDS of cas: 5388-42-1 This article mentions the following:

An efficient and environmentally friendly catalytic route for the reductive amination of carbonyl compounds has been designed. First, a one-pot procedure has been followed for the synthesis and incorporation of gold nanoparticles (AuNPs) into a mesoporous silica solid by using light as an abundant and clean energy source. Then, the as-prepared material has been successfully employed as a heterogeneous catalyst in the production of secondary and tertiary amines by reductive amination using Ph(Me)2SiH as the reducing agent. The endurance of the catalyst has been demonstrated in batch, and a continuous flow process allowing the safe preparation of multigram amounts of reductive amination products (accumulated TON = 434 in 18 h operation involving 6 sequential examples) has been implemented. The scope of the reaction has also been extended to the synthesis of more challenging active pharmaceutical ingredients (APIs), such as indoprofen precursors and biomass-derived products, which were obtained in good to excellent yields. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1SDS of cas: 5388-42-1).

Muvvala, Subhashini et al. published their research in ChemistrySelect in 2022 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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: 2-Phenylisoindolin-1-one

Microwave-Assisted Reductive Amination of 2-Carboxybenzaldehydes with Amines for the Synthesis of N-Substituted Isoindolin-1-ones was written by Muvvala, Subhashini;Kumari, Krishnaiah;Miriyala, Venkatesh;Mogili, Padma;Chidara, Sridhar;Maddirala, Shambabu Joseph;Saxena, Abhishek;Behera, Manoranjan. And the article was included in ChemistrySelect in 2022.Name: 2-Phenylisoindolin-1-one This article mentions the following:

Microwave-assisted, transition metal free methodol. for the synthesis of N-substituted isoindolin-1-ones I [R¹ = H, F; R² = i-Pr, Ph, PhCH₂, 2-(piperidin-1-yl)ethyl, etc.] from 2-carboxybenzaldehydes II and various amines R²NH₂ by reductive amination reaction using formic acid has been described. This method is relatively simple, benign, safe and tolerates a variety of functional groups. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Porobic, Ivana et al. published their research in Bioorganic & Medicinal Chemistry in 2013 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) 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.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

Molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid: A QSPR study was written by Porobic, Ivana;Kontrec, Darko;Soskic, Milan. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

Three molecularly imprinted polymers (MIPs) were prepared using the phytohormone indole-3-acetic acid (IAA) as a template mol., 4-vinylpyridine (MIP-1 and MIP-2) or N,N-dimethylaminoethyl methacrylate (MIP-3) as functional monomers, ethylenglycol dimethacrylate as a cross linker and acetonitrile (MIP-1), a methanol-water mixture (MIP-2) or chloroform (MIP-3) as porogens. Retention factors for IAA and 29 indole derivatives were determined by high-performance liquid chromatog., using the molecularly imprinted polymers as stationary phases and acetonitrile as an eluent. High correlations between selectivity factors of above mentioned polymers indicate that their retention mechanisms are basically the same. A quant. structure-property relationships anal. revealed that the presence of the terminal carboxyl group on the 3-side chain plays an essential role in the binding of the indole derivatives to the polymers. The derivatives without the carboxyl group exhibit a drastically lower affinity toward the polymers. Another factor which favors the binding is electronic d. of indole nucleus. Substituents with electro-withdrawing properties enhance the binding, while electro-donating substituents have the opposite effect. The length of the 3-side chain also affects the binding. Indole-3-carboxylic acid having the carboxyl group directly attached to the ring as well as the derivatives whose side chain is longer than that of IAA bind to the polymers with a lower affinity. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

Baykal, Aslihan et al. published their research in European Journal of Organic Chemistry in 2020 | CAS: 210345-56-5

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) 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.Recommanded Product: 210345-56-5

A Bu₄N[Fe(CO)₃(NO)]-Catalyzed Hemetsberger-Knittel Indole Synthesis was written by Baykal, Aslihan;Plietker, Bernd. And the article was included in European Journal of Organic Chemistry in 2020.Recommanded Product: 210345-56-5 This article mentions the following:

The nucleophilic Fe complex Bu₄N[Fe(CO)₃(NO)] (TBA[Fe]) catalyzes the direct intramol. amination of aryl vinyl azides RCH=C(N₃)C(O)R¹ (R = 3,4-dimethoxyphenyl, 4,5-dimethylfuran-2-yl, naphthalen-1-yl, etc.; R¹ = Ph, OMe, morpholin-4-yl, etc.) to give the corresponding indole derivatives I (R² = H, F, CN, dimethylaminyl, etc.; R³ = H, Br, OMe; R⁴ = H, Br, Me, OMe; R³R⁴ = -(CH=CH-CH=CH)-; R⁵ = H, Me), Me 2,3-dimethyl-4H-furo[3,2-b]pyrrole-5-carboxylate and Me pyrazolo[1,5-a]pyridine-2-carboxylate in good to excellent yields. 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).

Peters, A. T. et al. published their research in Journal of the Chemical Society in 1948 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 2-Phenylisoindolin-1-one

Reaction of certain diazosulfonates derived from 2-naphthol-1-sulfonic acid. XXVI. Phthalazine and isoindolinone compounds derived from aniline was written by Peters, A. T.;Rowe, F. M.;Brodrick, C. I.. And the article was included in Journal of the Chemical Society in 1948.Name: 2-Phenylisoindolin-1-one This article mentions the following:

PhN₂Cl (from 100 g. PhNH₂), added to an ice-cold solution of 400 g. 50% 2,1-HOC₁₀H₆SO₃Na in 1200 cc. H₂O, the 2-naphthol-1-benzenediazosulfonate (salted out with NaCl) converted by 100 g. Na₂CO₃ in 400 cc. H₂O at 0闂?to Na 1-benzeneazo-2-naphthoquinone-1-sulfonate (I), the mixture (after 15 min.) treated at 5闂?with 100 g. NaOH in 300 cc. H₂O, and then (after 15 min.) acidified with HCl at a temperature below 10闂? gives a tar which, on solution in NH₄OH and addition to boiling dilute HCl, gives 63% 1-hydroxy-3-phenyl-3,4-dihydro-4-phthalazineacetic acid (II), m. 264闂?(decomposition); Et ester, m. 91-2闂? boiling with Ac₂O 4 hrs. gives the O-acetate, m. 183闂? boiling with Ac₂O and a little C₅H₅N 50 hrs. gives also 4% of the internal anhydride of II, C₁₆H₁₂O₂N₂, m. above 320闂? 1-Keto-3-phenyl-2-methyltetrahydro-4-phthalazineacetic acid, m. 184-6闂? II (7 g.) and 15 cc. fuming HCl, heated 1 hr. at 180闂?and the product heated 10 min. with 15% Na₂CO₃, give 97% 3-phenyl-1-phthalazone (III), m. 208闂? turns green on standing (HCl salt, m. 162-4闂? picrate, yellow, m. 226闂?; Me₂SO₄ at 80闂?gives a resin which, boiled 5 min. with EtOH, gives the compound C₁₇H₁₈O₂N₂, m. 86-7闂? heated 4 hrs. at 140闂? this yields a compound C₁₆H₁₂ON₂, yellow, m. 234闂?(decomposition). III (2 g.), 140 cc. HCl, 80 cc. H₂O, 40 cc. EtOH, and 200 g. Zn-Hg, heated 4 hrs. at 70-80闂? give 85% 2-phenylphthalimidine. II (10 g.) in 70 cc. AcOH at 20闂? treated (2 hrs.) with 4 g. CrO₃ in 20 cc. AcOH and 10 cc. H₂O and the mixture kept overnight, gives 35.9% 3-phenyl-4-methyl-1-phthalazone (IV), m. 235闂?(picrate, yellow, m. 197闂?; 2 g. IV and 4 g. Na₂S₂O₄ in dilute aqueous NaOH, boiled 10 min., give 44.7% 1-keto-3-phenyl-4-methyltetrahydrophthalazine, m. 171闂? IV (3 g.), 70 cc. HCl, 50 cc. H₂O, and 90 g. Zn-Hg, boiled 4 hrs., give 2-phenyl-3-methylphthalimidine, m. 80闂? II (10 g.), added (30 min.) to 70 cc. HNO₃ at below 10闂?and the mixture poured onto ice, gives 73.6% of the 4′-NO₂ derivative of IV. II, refluxed 40 min. with aqueous H₂SO₄ (b. 140闂? or with equal volumes of H₂SO₄ and AcOH, gives 3-phenyl-1-phthalazone-x-sulfonic acid, prismatic needles with no m.p. I (from 50 g. PhNH₂) in aqueous Na₂CO₃ at 0闂? added to 50 g. NaOH in 180 cc. H₂O at 0闂? the mixture acidified after 5 min., the Na salt hydrolyzed, the acid solution evaporated to dryness, and the product extracted with and fractionated from AcOEt, gives 6.6 g. I; the more soluble fraction, boiled 5 min. with Ac₂O, gives 1.3 g. 2,5-diketo-3-phenylisoindolinopyrazolidocoline, m. 220-1闂? the 2,4-dinitrophenyl derivative m. 238-9闂?(cf. C.A. 42, 4568d). In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Name: 2-Phenylisoindolin-1-one).

Zhou, Feng et al. published their research in Zhongguo Yiyao Gongye Zazhi in 2013 | CAS: 320734-35-8

7-Bromooxindole (cas: 320734-35-8) 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 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). Computed Properties of C8H6BrNO

Synthesis of substituted 1,3-dihydroindolin-2-ones was written by Zhou, Feng;Zheng, Canhui;Zhu, Ju;Liu, Jia;Zhou, Youjun. And the article was included in Zhongguo Yiyao Gongye Zazhi in 2013.Computed Properties of C8H6BrNO This article mentions the following:

The substituted 1,3-dihydroindolin-2-one compounds 1a-1k, the intermediates of tyrosine kinase inhibitors such as sunitinib, were synthesized from substituted anilines by acylation and cyclization to give substituted isatin derivatives followed by reduction with triethylsilane/trifluoroacetic acid. In the experiment, the researchers used many compounds, for example, 7-Bromooxindole (cas: 320734-35-8Computed Properties of C8H6BrNO).