Indolyl acetic acid

Benzoyl chloride and derivatives acylate 2-amino-4-aryithiazoles in dioxane in yields of 80 to 90% (249, 250). The location of the acyl group on the exocyclic N has been demonstrated by the fact that the benzoyla-tion product is identical to the benzamidothiazole synthesized from benzamide and 2-bromothiazole (251). 3-Indolyl acetic acid chloride (89) acylates 2-aminothiazole in pyridine (Scheme 62) (81). 

A (Alternative) JCS 3175(1952). 2 g 3-indolyl-acetic acid (preparation given elsewhere here), 1.55 g freshly fused sodium acetate, 5 ml acetic anhydride. Heat 135-140° on oil bath for eighteen hours cool, wash with water and extract with CHCl3-ether (1 4). Wash organic phase with 3X20 ml saturated KHC03 and dry, evaporate in vacuum to get the l-acetyl-3-indolyl-acetone, which can be reduced to the alpha-methyl-tryptophol derivative with lithium aluminum hydride, and then converted to the dialkyl-tryptamine as already described (as can (I)), or used in step B, or reduced to (I) as follows dissolve 1 g in 1 ml 1 N Na-methoxide in methanol and 60 ml methanol, and keep at 40° for 10 minutes acidify with dilute HC1 and extract with ether. Dry, evaporate in vacuum to get (I) (recrystallize-methanol). 

Dicyclohexylcarbodiimide 2-Methyl-5-methoxy-3-indolyl acetic acid... 

Calatayud,]. M., Ascengao, J. G., and]. R. Albert-Garcia. 2006. FIA-fluorimetric determination of the pesticide 3-indolyl acetic acid. J. Fluoresc. 16 61-67. 

Benzyloxy-3-indolylacetic acid stirred with PGI5 in ice-cooled abs. ether until a soln. results, then a mixture of anhydrous methylamine and ether added dropwise, and allowed to stand 30 min. at room temp. 4-benzyloxy-3-indolyl-acetic acid methylamide. Y 86%. F. Troxler, F. Seemann, and A. Hofmann, Helv. 42, 2073 (1959). 

Similarly, 2-iodoanilides of indolyl acetic acid 15 lead to the corresponding 7,12-dihydroindolo[3,2-d][l]benzazepin-6(5H)-ones 16 (Equation (3) (2005TL8177)). Contrary to N-phenylsulfonyl derivatives lla,b and EOM protected species 13a,c, Boc-derivatives 14b and 15a do not tolerate these reaction conditions, and their fast decomposition has been observed. 

Oxidase, p-indolyl-acetic acid Call Tiss Oxidase, indole-acetic acid Stem pith 584 Palmitic acid, methyl ester Lf, Rt, St, Bk,... 

Activation effects have been described for other lipases. Thus milk lipase is stabilized and activated by glutathione and hydroquinone (330), serum lipase by sodium hexametaphosphate (331), tissue lipases by phosphate (332), and castor bean lipase is activated by strychnine (333) and by plant growth stimulants such as a-indolyl acetic acid and 2,4-dichlorophenoxyacetic acid (334). 

Winter A (1966) A hypothetical route for the biogenesis of lAA. Planta 71 229-239 Wright STC (1961) A sequential growth response to gibberellic acid, kinetin, and indolyl-acetic acid in the wheat coleoptile. Nature 190 699-700 Zimmerman DC, Coudron CA (1979) Identification of traumatin, a wound hormone, as 12-oxo-trans-lO-dodecanoic acid. Plant Physiol 63 536-541... 

Bourbouloux A, Bonnemain JL (1979) The different components of the movement and the areas of retention of labelled molecules after application of [ H]-indolyl-acetic acid to the apical bud of Vida faba. Physiol Plant 47 260-268 Bourbouloux A, Bonnemain JL, Vasseur J (1973) Caracteristiques du transport dans la tige de rauxine- C en provenance de jeunes feuilles de Vida faba L. CR Acad Sci Paris Ser D 276 501-504... 

Indole is the compound whose ring is present in tryptophan. It is also present in the natural auxin a-indolyl-acetic acid, a substance produced at the level of the apical bud and of the young leaves in plants, and transported to the region of the stem when growth takes place. 

The propargyhc esters 33 of (fS-indolyl)acetic acid undergo Au(I)/Ag(I)-catalyzed isomerization to the tetracyclic lactone 34, which is interpreted as a tandem (3,3)-sigmatropic oxa-CopE rearrangement followed by an intramolecular (2 + 2)-cydoaddition [155] ... 

Indolessigsaure indolyl acetic acid, indoleacetic acid (lAA)... 

Fig. 160. lAA = Indole - 3 - acetic acid = j8- Indolyl-acetic acid. 

Sulfonation of indole with pyridinium-A -sulfonate yields indolyl-3-sulfonic acid, and bromine in pyridine at 0 °C affords 3-bromoindole (Scheme 7.4). Acetylation with a heated mixture of acetic anhydride and acetic acid gives 1,3-diacetylindole. Methylation requires heating with methyl iodide in DMF (A,A-dimethylformamide) at 80-90 C and yields 3-methylindole. This compound reacts further, giving 2,3-dimethylindole and finally l,2,3,3-tetramethyl-3Ff-indoleninium iodide. 

A synthesis of the antitumor agent elliptidne has utilized the indolyl-substituted oxazole (351) as a key intermediate (77JOC2039). Diels-Alder reaction of (351) with acrylonitrile in acetic acid afforded a pyridinecarbonitrile (352) which was reacted with methyllithium, and the ketimine salt was hydrolyzed and cyclized to ellipticine (353 Scheme 76). Other Diels-Alder reactions of this type, particularly intramolecular cycloadditions of oxazoles with alkenic dienophiles should provide rapid access to a variety of alkaloid systems. 

The latter was added to 15 ml of 1-phenylpiperazine and the mixture heated at 140-160°C for one hour and twenty minutes. The cooled mixture was triturated with 100 ml of ether, filtered, and the ether filtrate concentrated to dryness. The residue was mixed with water and acetic acid, the pH adjusted to about 5.0, and the insoluble material was collected by filtration giving 5 g of crude product which was recrystallized from methanol to give 2.2 g of l-[2-(2-carbethoxy-5,6-dimethoxy-3-indolyl)ethyl]-4-phenylpiperazine, M.P. 142.5-144.0°C. 

A cold, stirred solution of 1-phenyl-piperazine in tetrahydrofuran was treated all at once with [3-(2-methyl-5,6-dimethoxy)indolyl]glyoxalyl chloride. There was an immediate voluminous precipitate of a white crystalline solid which was removed by filtration. The filtrate was taken to dryness and the residual light brown gum was stirred and shaken with water, ethyl acetate and acetic acid. The mixture was warmed on a steam bath and the resulting solid was collected after cooling in an ice bath thus affording l-[(3-(2-methyl-5,6-dimethoxy)indolyl)glyoxalyl]-4-phenylpiperazine as a near white solid, melting point 163°-174°C. 

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