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Bartoli indole synthesis - Wikipedia

After the N-H proton, the hydrogen at C-2 is the next mostacidic proton on indole. Reaction of N-protected indoles with or results in lithiation exclusively at the C-2 position. This strongnucleophile can then be used as such with other electrophiles.

Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of Avrainvillamide.

Reaction of indole-3-carboxaldehydes 4 with hydrazine derivatives and different substituted acid hydrazides afforded the corresponding hydrazine derivatives 5a-c and acid hydrazide derivatives 7-11 respectively. Condensation of indole-3-carboxaldehydes 4 with phenacyl bromide and thiourea gives 1,3-thiazol-2-amine derivative 18. On the other hand, reaction 4 with 3-acetylchromene-2- one afforded chalcone derivative 19. Compound 4 undergoing Knoevenagel condensation with cyanoacetamide, ethyl cyanoacetate, benzimidazol-2-ylacetonitrile, rhodanine-3-acetic acid, 2,3- dihydropyrimidin-4-one derivative and 2,4-dihydropyrazol-3-one afforded the compounds 20a,b, 22, 23, 27 and 28 respectively. The structure of the newly synthesized compounds has been confirmed by elemental analysis and spectra data. The antimicrobial activities of the some newly synthesized compounds were measured and showed that most of them have high activities.

Fischer Indole Synthesis - Organic Chemistry Portal

The Hemetsberger indole synthesis (also called the Hemetsberger-Knittel synthesis) is a chemical reaction that thermally decomposes a 3-aryl-2-azido-propenoic ester into an indole-2-carboxylic ...

AB - Anhydrous indium trichloride (InCl3) is found to catalyze the electrophilic substitution reaction of indole with aromatic aldehydes and Schiff's bases which resulted in an efficient synthesis of bis- indolylmethanes in good to excellent yield.

Indole synthesis - Organic chemistry

His research areas include organic synthesis and polymer chemistry applied to nanoscience and nanotechnology with emphasis on the design, fundamental understanding, synthesis, and applications ...

Reactions are generally conducted between 200 and 500 °C. Yieldscan be as high as 60%. Other precursors to indole includeformyltoluidine, 2-ethylaniline, and 2-(2-nitrophenyl)ethanol, allof which undergo cylizations. Manyother methods have been developed that are applicable.

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Leimgruber–Batcho Indole Synthesis - Reaction …

The hydrazine derivatives 5a-c were obtained by the reaction of 1H-indole-3-carboxaldehyde derivative 4 with different substituted hydrazines [20] namely, hydrazine hydrate, phenyl hydrazine and 2-hydrazinyl-1,3- benzothiazole (Scheme 1). The molecular structure of the synthesis compounds were established based on analytical and spectral data. For example, 1H NMR spectrum of compound 5c showed an D2O -exchangeable signal at 7.95 and 11.82 assigned to the two NH protons and a non exchangeable signal at 8.42 ppm corresponding =CH proton. On other hand mass spectrum of 5c showed a molecular ion peak m/z at 447 corresponding to the molecular formula C22H15BrN4S.

Indole Alkaloid Synthesis via Radical Cascade Reactions

Reaction of 1H-indole-3-carboxaldehyde derivative 4 with different substituted acid hydrazides [21] such as 2-(quinolin-8-yloxy)acetohydrazide 6a, 2-(1H-indol-3-yl)acetohydrazide 6b, 4-(1H-indol-3-yl)butanehydrazide 6c and 1-benzofuran-2-carbohydrazide 6d in presence of catalytic amount of acetic acid in absolute ethanol

Indole Synthesis via SRN1 Reactions - Combinatorial …

A mixture of 1H-pyrazol-5(4H)-one (1.74 g, 0.01 mol) and 1H- indole-3-carboxaldehyde 4 (3 g, 0.01 mol) in acetic acid in the presence of anhydrous sodium acetate was refluxed for 5 h. The reaction mixture was cooled to room temperature and poured into ice cold water. The solid separated out was filtered washed with water and recrystallized from (ethanol/DMF) to give 28 as orange crystals. Yield (3.01g, 66%); m.p.: 190-192˚C. Anal. calcd. for C25H18BrN3O (456.33): C, 65.80; H, 3.98; Br,17.51; N, 9.21. Found: C, 65.56; H, 3.68; Br, 17.31; N, 9.00.

Shot description of article - Indole Synthesis via SRN1 Reactions

The most reactive position on indole for is C-3, which is 1013 times morereactive than . Forexample, of indolewill take place at room temperature exclusively at C-3. Since thepyrrollic ring is the most reactive portion of indole, nucleophilicsubstitution of the carbocyclic (benzene) ring can take place onlyafter N-1, C-2, and C-3 are substituted.

Chemical reactions of indole Basicity

Reaction 1H-indole-3-carboxaldehyde 4 with cyanoacetohydrazide in absolute ethanol [22] to form the N'- [1H-indol-3-ylmethylene]-2-cyanoacetohydrazide derivative 11. The assignment of the structure of compound

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