53918-89-1

Upstream product

• 78-93-3 butanone 
• 18312-46-4 (2-methoxyphenyl)hydrazine 
• 4091-39-8 3-chloro-2-butanone 
• 90-04-0 2-methoxy-phenylamine 
• 380383-87-9 N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester 
• 513-85-9 2.3-butanediol 

Relevant academic research and scientific papers

Improved indole syntheses from anilines and vicinal diols by cooperative catalysis of ruthenium complex and acid

By developing a new and efficient dinuclear catalyst [Ru(CO) 2(Xantphos)]2 [Xantphos = 4,5-bis(diphenylphosphino)-9,9- dimethyl-9H-xanthene], an improved synthesis of indole from vicinal diols and anilines by cooperative catalysis of ruthenium complex and p-TSA (para-toluenesufonic acid) has been demonstrated. The presented synthetic protocol allows assembling a wide range of products in an efficient manner. Comparing to the existed protocols, our indole syntheses can be achieved at lower reaction temperature, in shorter reaction time, and with improved substrate tolerance.

Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols

A straightforward and atom-economical method is described for the synthesis of 2,3-disubstituted indoles. Anilines and 1,2-diols are condensed under neat conditions with catalytic amounts of either [Cp*IrCl2] 2/MsOH or RuCl3·xH2O/phosphine (phosphine = PPh3 or xantphos). The reaction does not require any stoichiometric additives and only produces water and dihydrogen as byproducts. Anilines containing methyl, methoxy, chloro and fluoro substituents can participate in the cyclocondensation. Meta-substituted anilines give good regioselectivity for 6-substituted indoles, while unsymmetrical diols afford excellent regioselectivity for the indole isomer with an aryl or large alkyl group in the 2-position. The mechanism for the cyclocondensation presumably involves initial formation of the α-hydroxyketone from the diol. The ketone subsequently reacts with aniline to generate the α-hydroxyimine which rearranges to the corresponding α-aminoketone. Acid- or metal-catalysed electrophilic ring-closure with the release of water then furnishes the indole product.

Expedient synthesis of indoles from N-Boc arylhydrazines

The readily available N-Boc arylhydrazines undergo efficient Fischer cyclizations to provide the indoles in good yields, when reacted with enolizable ketones.

Hydroxyindole derivatives as inhibitors of IL-1 generation. II. Synthesis and pharmacological activities of (E)3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives

A series of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives was prepared and the inhibitory activities of its members on IL-1 generation were evaluated in an in vitro system using exudate cells from the rat carboxy-methyl cellulose (CMC) induced air-pouch model. All the compounds in this new series were found to be inhibitors of IL-1 generation. In particular, the methoxy-substituted 2-phenyl compounds 28d-f were the most potent inhibitors of IL-1 generation (eg, 28d: IC50 = 0.8 μ,M). The compounds in this series also inhibited IL-1α and IL-1β generations in an in vitro system using human monocytes stimulated with LPS (eg, 28b: IC50 = 1.4 μM (IL-1α) and 0.9 μM (IL-1β)).