Tag: M.W=250-300

Cavallini, G. published the artcileSome indole derivatives presumably of biological interest. II. Synthesis of 5-bromo-3-indolaldehyde, Recommanded Product: Ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate, the publication is Farmaco, Edizione Scientifica (1958), 113-16, database is CAplus.

Et pyruvate p-bromophenylhydrazone (I), m. 148-50°, was prepared in 90% yield. Heating slowly with stirring 10 g. I and 20 g. polyphosphoric acid until no heat was more developed, adding at 60° 50 cc. H₂O, filtering, washing, and drying gave 7 g. Et 5-bromo-2-indolcarboxylate (II), m. 164-5°. Refluxing II in KOH-80% EtOH and acidifying gave 90% of the free acid (III) m. 279-80° (after sublimation). Mixing 4 g. III with 0.8 g. Cu chromite, suspending in 20 cc. quinoline, and refluxing 2 hrs., pouring into H₂O acidified with HCl, extracting with Et₂O, washing, drying, and evaporating gave 2 g. 5-bromoindole, m. 85-6° (cyclohexane). Stirring 3.1 g. N-methylformanilide and 3.5 g. POCl₃ for 15 min., adding 15 g. C₂H₄Cl₂ and 5.4 g. II, refluxing 1 hr., pouring into 15 g. NaOAc in 30 cc. H₂O at 0°, decanting the H₂O, adding petr. ether, centrifuging, and drying gave 4 g. crude 5-bromo-2-carbethoxy-3-indolealdehyde (IV), m. 245° (EtOH); p-nitrophenylhydrazone, m. 360°. Adding to 0.68 g. KOH in 50 cc. 80% EtOH 2.4 g. IV refluxing 30 min., adding 0.85 g. PhNH₂, diluting the hot solution with 50 cc. H₂O, cooling to 0°, and acidifying with HCl gave 2.4 g. 5-bromo-3-(phenyliminomethyl)-2-indole-carboxylic acid (VII), m. 253°. Adding to a stirred mixture of 2 g. N-methylformanilide and 2.3 g. POCl₃ 10 g. C₂H₄Cl₂, cooling to 0°, adding dropwise 2 g. 5-bromoindole in 5 cc. C₂H₄Cl₂, avoiding a rise in temperature beyond 10°, refluxing 30 min., pouring the cooled mixture into 10 g. NaOAc in 20 cc. H₂O, removing the C₂H₄Cl₂ by steam distillation, diluting the solution to 300 cc., heating to boiling, filtering, and cooling gave 0.3 g. 5-bromo-3-indolealdehyde, m. 205° (H₂O); p-nitrophenylhydrazone, m. 273° (decomposition). The same compound is prepared in 200 mg. yield by heating to reflux 2 g. VII and 20 g. Me₂NPh until the liberation of CO₂ ceases, adding 100 cc. H₂O, distilling with steam to remove the Me₂NPh, diluting to 200 cc. with H₂O, and filtering.

Farmaco, Edizione Scientifica published new progress about 100123-25-9. 100123-25-9 belongs to indole-building-block, auxiliary class Indole,Bromide,Ester,Aldehyde, name is Ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate, and the molecular formula is C12H10BrNO3, Recommanded Product: Ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chauhan, Jyoti published the artcileBlue LED Mediated Intramolecular C-H Functionalization and Cyclopropanation of Tryptamines: Synthesis of Azepino[4, 5-b]indoles and Natural Product Inspired Polycyclic Indoles, Synthetic Route of 167015-84-1, the publication is Organic Letters (2020), 22(11), 4537-4541, database is CAplus and MEDLINE.

A novel blue LED mediated intramol. C-H functionalization of tryptamine derivatives to generate azepino[4, 5-b]indoles, e. g., I, in moderate to good yields is reported. By altering the substitution at the tryptamine nitrogen, intramol. cyclopropanation is achieved in high yields under the same reactions condition to provide natural product inspired polycyclic indoles, e. g., II, which are further transformed to spiropiperidino indoles, e. g., III, in decent yields. The mechanism of formation of the compounds was investigated through DFT studies.

Organic Letters published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Synthetic Route of 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Palani, Vignesh published the artcileA pyrone remodeling strategy to access diverse heterocycles: application to the synthesis of fascaplysin natural products, Name: 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, the publication is Chemical Science (2021), 12(4), 1528-1534, database is CAplus and MEDLINE.

The synthesis of diverse N-fused heterocycles, including the pyrido[1,2-a]indole scaffold, e.g., I, using an efficient pyrone remodeling strategy was described. The pyrido[1,2-a]indole core was demonstrated to be a versatile scaffold that could be site-selectively functionalized. The utility of this novel annulation strategy was showcased in a concise formal synthesis of three fascaplysin congeners.

Chemical Science published new progress about 683229-62-1. 683229-62-1 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Ether,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, and the molecular formula is C15H20BNO3, Name: 5-Methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Yates, C. G. published the artcileNew intermediates and dyes. X. Preparation and reactions of 2-n-alkylquinizarins, SDS of cas: 2642-37-7, the publication is Journal of the Chemical Society (1965), 626-9, database is CAplus.

2-Methylquinizarin was prepared by hydrolysis of 4-chloro-l-hydroxy-2 methylanthraquinone, or better, from 1,4-diamino-2-methylanthraquinone and aqueous alk. dithionite. 2-Propyl-, 2-butyl-, 2- hexyl-, 2-heptyl-, and 2-octylquinizarin were derived by the interaction of leucoquinizarin and an aliphatic aldehyde: this reaction appeared to be limited, as the use of decyl- and dodecylaldehyde gave quinizarin only. Inhibiting effects of the 2-n-alkyl groups in reactions with amines were examined Thus, 2-methyl-, propyl-, and butylquinizarin and aqueous NH₃ gave some disubstitution of the hydroxy groups, but with derivatives of longer alkyl chain, only monosubstitution occurred; MeNH₂ afforded yellow fluorescent products, probably formed by loss of water from 2-alkyl-1,4-bis(methylamino)anthraquinones. Whereas cyclohexylamine gave excellent yields of 2-alkyl-1,4-bis(cyclohexylamino)anthraquinones, disubstitution was inhibited in reactions with PhNH₂, which gave monoanilino derivatives

Journal of the Chemical Society published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C9H9ClN2, SDS of cas: 2642-37-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nakamura, Hiroshi published the artcileSensitive and specific detection of tryptophan, tryptamine and N-terminal tryptophan peptides on thin-layer plates using a unique fluorogenic reaction with fluorescamine, Recommanded Product: Potassium 1H-indol-3-yl sulfate, the publication is Journal of Chromatography (1978), 152(1), 153-65, database is CAplus.

Two sensitive and sp. methods were developed for the detection of tryptophan, tryptamine, N-terminal tryptophan peptides and other 3-(2-aminoethyl)-indoles on thin-layer plates in which the reaction is based on the unique fluorescence of the fluorescamine derivatives after treatment with HClO₄. The 1st method the compounds are separated on plates and reacted by dipping in acetone-n-hexane (1:4) containing fluorescamine, whereas in the 2nd method the compounds are first derivatized with fluorescamine at the origin of the plates by dipping in the solution and then separated When sprayed with 40% HClO₄, the fluorescamine derivatives appear as yellow-orange fluorescent spots. Certain 3,4-dihydroxyphenylethylamines and 3-methoxy-4-hydroxyphenylethylamines that have a free amino group in the side-chain also react, but they give a bluish fluorescence. Depending on the compounds, amounts of 1-800 pmole could be detected.

Journal of Chromatography published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Recommanded Product: Potassium 1H-indol-3-yl sulfate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nakamura, Hiroshi published the artcilePerchloric acid, a fluorogenic spray reagent for tryptophan, tryptamine, peptides containing tryptophan and other 3-substituted indoles, Application In Synthesis of 2642-37-7, the publication is Journal of Chromatography (1978), 152(1), 167-74, database is CAplus.

When silica gel plates containing 3-substituted indoles (e.g., 3-methylindole, indole-3-acetic acid), tryptophan derivatives, tryptamine, and tryptophan-containing peptides (e.g., H-Trp-Gly-OH, H-Pro-Trp-OH, H-Lys-Trp-Lys-OH) were sprayed with 70% HClO₄, a strong yellow-orange fluorescence developed. Other indole derivatives did not give this fluorescence when sprayed with 70% HClO₄. 3-Substituted indoles can be detected at 40-850 pmole by this method.

Journal of Chromatography published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Application In Synthesis of 2642-37-7.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Li, Hua published the artcileModified metabolites mapping by liquid chromatography-high resolution mass spectrometry using full scan/all ion fragmentation/neutral loss acquisition, Safety of Potassium 1H-indol-3-yl sulfate, the publication is Journal of Chromatography A (2019), 80-87, database is CAplus and MEDLINE.

Modified metabolites play important roles in diagnostic monitoring, oxidative response and physiol. regulation. Comprehensive anal. methods are greatly needed for improving the coverage of modified metabolites and studying their physiol. function. Here, a novel nontargeted profiling method for mapping modified metabolites was developed by liquid chromatog.-high resolution mass spectrometry with full scan/all ion fragmentation/neutral loss (FS/AIF/NL) data acquisition. Modified metabolites were unbiasedly defined with less false pos. results by mixed standards verification. Thirteen types of modified metabolites in urine were analyzed at the same time, and 198 of 307 modified metabolites at pos. mode and 166 of 366 modified metabolites at neg. mode were putatively identified. The modified metabolites profiling method was applied for investigating the metabolic differences between the patients with breast cancer and health controls. As a result, many modified metabolites with glucuronidation, ribosylation and indole acetylation modification were significantly up-regulated in breast cancer and four modified metabolites including 7-methylguanosine, N₄-acetylcytidine, dihyroxy-1H-indole glucuronide I and indole-3-acetic acid-O-glucuronide were identified as potential biomarkers for the diagnose of breast cancer.

Journal of Chromatography A published new progress about 2642-37-7. 2642-37-7 belongs to indole-building-block, auxiliary class Indole,Salt,Sulfonate,Inhibitor,Inhibitor, name is Potassium 1H-indol-3-yl sulfate, and the molecular formula is C8H6KNO4S, Safety of Potassium 1H-indol-3-yl sulfate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

White, James D. published the artcileTandem Intramolecular Photocycloaddition-Retro-Mannich Fragmentation as a Route to Spiro[pyrrolidine-3,3′-oxindoles]. Total Synthesis of (卤)-Coerulescine, (卤)-Horsfiline, (卤)-Elacomine, and (卤)-6-Deoxyelacomine, Safety of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Journal of Organic Chemistry (2010), 75(11), 3569-3577, database is CAplus and MEDLINE.

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramol. [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3′-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient cyclobutane. The tandem intramol. photocycloaddition-retro-Mannich process, abbreviated as TIPCARM, leads to a spiropyrrolidine which is poised to undergo a second retro-Mannich fragmentation that expels the malonate unit and generates transiently an indolenine. The latter undergoes rearrangement to a 尾-carboline, which upon brominative oxidation undergoes further rearrangement to an oxindole. With tryptamine as starting material, the entire sequence leads to the alkaloid (卤)-coerulescine (I, R = H). Starting from 5-methoxytryptamine, a parallel series affords (卤)-horsfiline I (R = MeO). Modification of the malonylidene unit to include an iso-Bu substituent at C3 affords a photosubstrate which also undergoes the TIPCARM process. In this case, a 2′-isobutyl-substituted spiro[indoline-3,3′-pyrrolenine] results. This undergoes stereoselective hydride reduction to give a product with relative orientation at the spiro carbon and the new stereocenter bearing the iso-Bu appendage corresponding to that of the alkaloid elacomine. From tryptamine, the sequence paralleling that leading to coerulescine and horsfiline terminates at 6-deoxyelacomine, whereas 6-methoxytryptamine as starting material affords (卤)-elacomine (II) itself.

Journal of Organic Chemistry published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C7H16Cl2Si, Safety of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

White, James D. published the artcileSynthesis of the ABCD ring system of Vinca alkaloids using tandem intramolecular [2 + 2]-photocycloaddition-retro-Mannich fragmentation, HPLC of Formula: 167015-84-1, the publication is Heterocycles (2014), 88(2), 899-910, database is CAplus.

Irradiation of 3-alkylindole (E)- and (Z)-I gave spiropyrroline II via [2+2]-photocycloaddition and subsequent in situ retro-Mannich fragmentation of a fused cyclobutane. N-Alkylation of II followed by treatment of the resulting pyrrolinium salt with sodium hydride and lithium diisopropylamide generated a dienolate dianion which underwent cyclization to afford tetracyclic products, e.g., III. The configuration of III was proven by a series of NMR experiments which established that ring C in the major stereoisomer resides in a boat conformation. The prepared tetracycles contain structural features including the ABCD ring system and substituents found in certain alkaloids of the Vinca family.

Heterocycles published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C6H10O7, HPLC of Formula: 167015-84-1.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Mu, Xin-Peng published the artcileStereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, the publication is Angewandte Chemie, International Edition (2021), 60(20), 11211-11216, database is CAplus and MEDLINE.

A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones such as I to yield cycloheptaindoles such as II. Exptl. and computational studies suggested that the reaction is a photoredox process initiated by single-electron oxidation of enaminones, which undergo subsequent cyclobutane formation and rapid fragmentation of the intermediate radical cations to form cyclohepta[b]indoles.

Angewandte Chemie, International Edition published new progress about 167015-84-1. 167015-84-1 belongs to indole-building-block, auxiliary class Indols, name is tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate, and the molecular formula is C15H20N2O2, Application of tert-Butyl 3-(2-aminoethyl)-1H-indole-1-carboxylate.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles