Indole , with acetic acid

Pyrano[3,4-b]indol-3-ones are the most useful equivalents of the indol-2,3-quinodimethane synthon which are currently available for synthetic application. These compounds can be synthesized readily from indole-3-acetic acids and carboxylic anhydrides[5,6]. On heating with electrophilic alkenes or alkynes, adducts are formed which undergo decarboxylation to 1,2-dihydro-carbazoles or carbazoles, respectively. 

M. E. Brown, R. M. Jack.son, and S. K. Burlingham, Effects produced on tomato plants by seed or root treatment with gibberellic acid and indol-3yl-acetic acid. Journal of Experimental Botany /9 544 (1968). 

According to another approach, treatment of A-[2-(indol-3-yl)ethyl]-l,2,5,6-tetrahydropyridine (137), obtained from the corresponding pyridinium salt 136 by borohydride reduction, first with potassium rerf-butoxide, and then with acetic acid, led to ( )-l via key intermediate 135 in 78% yield (102). 

A 3-1. stainless steel, rocking autoclave (Note 1) is charged with 270 g. (4.1 moles) of 85% potassium hydroxide and 351 g. (3.00 moles) of indole (Note 2), and then 360 g. (3.3 moles) of 70% aqueous glycolic acid is added gradually (Note 3). The autoclave is closed and rocked at 250° for about 18 hours (Note 4). The reaction mixture is cooled to below 50°, 500 ml. of water is added, and the autoclave is rocked at 100° for 30 minutes to dissolve the potassium indole-3-acetate. The aqueous solution is cooled to 25° and removed from the autoclave, the autoclave is rinsed out well with water, and water is added until the total volume of solution is 3 1. The solution is extracted with 500 ml. of ether (Note 5). The aqueous phase is acidified at 20-30° with 121V hydrochloric acid and then is cooled to 10° (Note 6). The indole-3-acetic acid that precipitates is collected on a Buchner funnel, washed with copious amounts of cold water, and dried in air or a vacuum desiccator out of direct light (Note 7) weight 455-190 g. (87-93%) m.p. 163-165° (dec.). 

This is the most convenient method of preparing indole-3-acetic acid if an agitated autoclave is available. The method can be used to prepare other indole-3-acetic acids from a-hydroxy acids. For example, a-methylindole-3-acetic acid has been prepared by condensing indole with lactic acid. 

Indole-3-acetic acid has been prepared by the Fischer indole synthesis,2 by hydrolysis of indoleacetonitrile,3 from the reaction of gramine-type compounds with cyanide ion under conditions... 

To 21.6 g phenylhydrazine dissolved in 300 ml 0.3N sulfuric acid, add 9.8 g concentrated sulfuric acid. Add dropwise with stirring and heating at 100°, 11.6 g methyl-beta-formyl-propionate in 300 ml 0.3 N sulfuric acid and continue heating six hours to get 14 g indole-3-acetic acid. Convert to the dialkyltryptamine as already described. 

It is important to keep in mind that any extraction of organic matter from soil will include both naturally occurring organic matter and organic contaminants. Separating the two at some later stage of analysis is thus an essential analytical step. For example, extraction of soil with hexane or dichloromethane will extract both l,l,l-trichloro-2,2-di(4-dicholorphenyl)ethane (DDT), a contaminant, and octadecanoic acid, a natural fatty acid. Also, the herbicide 2,4-dichlorophenoxy acetic acid, a contaminant, and indole-3-acetic acid, a natural plant hormone, are both extracted by water (see Figure 12.3). These... 

Structural information on aromatic donor molecule binding was obtained initially by using H NMR relaxation measurements to give distances from the heme iron atom to protons of the bound molecule. For example, indole-3-propionic acid, a structural homologue of the plant hormone indole-3-acetic acid, was found to bind approximately 9-10 A from the heme iron atom and at a particular angle to the heme plane (234). The disadvantage of this method is that the orientation with respect to the polypeptide chain cannot be defined. Other donor molecules examined include 4-methylphenol (p-cresol) (235), 3-hydroxyphenol (resorcinol), 2-methoxy-4-methylphenol and benzhydroxamic acid (236), methyl 2-pyridyl sulfide and methylp-tolyl sulfide (237), and L-tyrosine and D-tyrosine (238). Distance constraints of between 8.4 and 12.0 A have been reported (235-238). Aromatic donor proton to heme iron distances of 6 A reported earlier for aminotriazole and 3-hydroxyphenol (resorcinol) are too short because of an inappropriate estimate of the molecular correlation time (239), a parameter required for the calculations. Distance information for a series of aromatic phenols and amines bound to Mn(III)-substituted HRP C has been published (240). 

Indole-3-Acetic Acid. Dissolve 21.6 g of phenylhydrazine in 300 ml 0.3 N sulfuric acid. To this solution add 9.8 g of coned sulfuric acid. With stirring and heating to 100°, add dropwise 11.6 g of methyl-beta-formyl-propionate in 300 ml of 0.3 N sulfuric acid. Continue the heating and gentle stirring for 6 hours to get about 14 g of indole-3-acetic acid. This is from CA, 72, 66815 (1970). 

When subjected to drought stress, excised wheat Triticum aestivum L.) leaves increase ethylene production as a result of an increased synthesis of ACC 71 and an increased activity of the ethylene-forming enzyme (EFE) which catalyzes the conversion of ACC 71 to ethylene. Rehydratation to relieve water stress reduces EFE activity to levels similar to those in non-stressed tissue. Pretreatment of the leaves with N-benzyladenine (BA) 75 or indole-3-acetic acid lAA 76 prior to drought stress caused further increase in ethylene production. Conversely, pretreatment of wheat leaves with abscisic acid ABA 77 reduced ethylene production to levels of non-stressed leaves, accompanied by a decrease in ACC 71 content, Eq. (29). 

Protonation of indole has been shown to give the indoleninium (3H-indolium) cation, and this is presumably formed under the conditions commonly used for electrophilic substitution reactions in the benzene series. For indole these conditions are often unsatisfactory and, for example, nitration of indole with nitric acid gives polymers. On the other hand, A/ -alkylindoles can be nitrated with concentrated nitric acid and acetic anhydride at -70 °C to afford l-alkyl-3-nitroindoles. 

DC031 Knypl, J. S., K. M. Chylinska, and M. W. Brzeski. Increased level of chloro-genic acid and inhibitors of indole-3-acetic acid oxidase in roots of carrot infested with the northern root-knot nematode. Physiol Plant Pathol 1975 6 51. 

Reaction of desoxyanisoin (11-1) with phenylhydrazine goes in a straightforward manner to hydrazone (11-2). Treatment of that intermediate with acetic acid leads to the formation of the indole ring and the formation of indoxole (11-3) [10]. 

Indolines are produced in good yield from 1-benzenesulfonylindoles by reduction with sodium cyanoborohydride in TFA at 0°C (Equation 5) (89TL6833). If acyl groups are present at C-2 or C-3 in the substrate, they are reduced to alkyl groups. Indole is also reduced to 2,3-dihydroindole by sodium cyanoborohydride and acetic acid or triethylamineborane and hydrochloric acid. An alternative method for preparing indolines involves treatment of indoles with formic acid (or a mixture of formic acid and ammonium formate) and a palladium catalyst (82S785). Reduction of the heterocyclic ring under acidic conditions probably involves initial 3-protonation followed by reaction with hydride ion. 

Yu and Wang431 considered that indole-3-acetic acid exerts its stimulating effect on expansion growth by inducing the synthesis of the enzyme catalyzing the conversion of S-adenosylmethionine into ACC, a conclusion at variance with the suggestion of Vioque and coworkers432 that indoleacetic acid oxidase and its substrate (IAA) participate in the last reaction in the ethylene biosynthesis pathway, namely, the formation of ethylene from ACC. 

Mixed Cytokinins. The first cytokinin, kinetin [525-79-1] (3), was isolated from stale herring sperm (8) but, like so many biologically active natural products, it was later found in the vascular system of tobacco stems and leaves (9). Yeast also proved to have a very high titre of kinetin (see Yeasts) (8). The compound is very active in increasing cell division in tobacco wound callus tissue that has been cultured on White s agar medium supplemented with 2 mg/L of indole-3-acetic acid (IAA) [87-51 -4], The presence of IAA is mandatory to induce cell division in the presence of kinetin. 

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