552333-33-2

Usage

Derivative of coumarin

A naturally occurring organic compound found in many plants.

Pharmacological activities

Potential anti-viral, anti-inflammatory, antioxidant, and antimicrobial properties.

Potential use

Treatment of various diseases.

Building block

Used in the synthesis of other organic compounds with potential medicinal applications.

Versatile chemical

Promising pharmaceutical and biological activities.

Upstream product

• 89-51-0 Homophthalic acid 
• 19725-82-7 5-Bromo-2-carboxymethyl-benzoic acid 
• 75-36-5 acetyl chloride 

Downstream Products

• 1355049-16-9 methyl [2-(azidocarbonyl)-4-bromophenyl]acetate 
• 1355049-18-1 methyl {2-[(anilinocarbonyl)amino]-4-bromophenyl}acetate 
• 1355049-21-6 6-bromo-2-hydroxy-N₁,N₃-diphenyl-1H-indole-1,3-dicarboxamide 
• 99365-40-9 6-bromo-2,3-dihydro-1H-indole-2-one 
• 1355049-19-2 C₁₀H₈BrNO₃ 
• 1370022-16-4 (3R,4R)-methyl 7-bromo-1-oxo-3-phenylisochroman-4-carboxylate 
• 1370022-13-1 C₁₆H₁₁BrO₄ 
• 1313051-55-6 (R)-2-(2-methylphenyl)propan-1-ol 
• 1610724-56-5 (2'R,3'S,4'R)-1-tert-butyl 4'-methyl 7'-bromo-1',2-dioxo-3'-phenyl-3',4'-dihydro-1'H-spiro[indoline-3,2'-naphthalene]-1,4'-dicarboxylate 

Relevant academic research and scientific papers

Highly Enantio- and Diastereoselective Catalytic Asymmetric Tamura Cycloaddition Reactions

The first broad-scope catalytic asymmetric Tamura cycloaddition reactions are reported. Under the influence of anion-binding bifunctional catalysis a wide range of α,β-unsaturated N-trityl imines undergo reactions with enolisable anhydrides to form highly synthetically useful α-tetralone structures with excellent enantio- and -diastereocontrol. In stark contrast to the previous literature benchmarks, doubly activated or highly electron deficient alkenes are not required. A facile two-step, high yielding sequence can convert the cycloadducts to α-haloketones (challenging to generate catalytically by other means) with the net formation of two new C?C bonds and three new contiguous stereocentres with exquisite stereocontrol. A DFT study has provided insight into the catalyst mode of action and the origins of the observed enantiocontrol.

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.

Catalytic asymmetric tamura cycloadditions

In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 °C and -30 °C delivering products epimeric at one stereocenter only, in near optical purity. Squared away: The first strategy for bringing about enantioselective Tamura reactions is reported. In the presence of a squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products with excellent enantio- and diastereocontrol. The methodology is of wide scope and leads to structurally diverse products.

Enantioselective organic anhydride reactions

Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C4-C50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.

Synthesis of fused tetrazolone derivatives

New fused tetrazolone derivatives were synthesized using homophthalic and maleic anhydrides. Treatment of anhydrides with trimethylsilyl azide opened the lactone rings and formed the corresponding intermediates, which bore 1,3-dipole and dipolarophile functionalities in ortho positions. The intermediates partially underwent internal 1,3-dipolar cycloaddition to produce fused tetrazolone derivatives. When the carbonyl groups in anhydride were not conjugated with any double bond, then a triazine-fused tetrazolone derivative was formed. TUeBITAK.

ENANTIOSELECTIVE ORGANIC ANHYDRIDE REACTIONS

Disclosed herein is enantioselective synthetic method comprising reacting an enolisable C4-C50 organic anhydride with a second compound selected from the group consisting of an aldehyde, a ketone, an aldimine, a ketimine or a Michael Acceptor in the presence of a bifunctional organocatalyst. The reaction may find particular utility in the enantioselective synthesis of medicinally relevant heterocycles, such as dihydroisocoumarins and dihydroisoquinolinones.

A catalytic asymmetric reaction involving enolizable anhydrides

In the presence of a highly efficient novel bifunctional organocatalyst at low loadings under mild conditions, enolizable homophthalic anhydrides can be added to a range of aromatic and aliphatic aldehydes to give dihydroisocoumarins, with excellent yields and diastereo-and enantiocontrol (up to 99% ee).

A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles

The one-pot, three-component reaction of substituted homophthalic anhydrides with hydrazine in DMF as solvent and reactant, at reflux temperature, afforded isochromeno[3,4-c]pyrazole-5(2H)-one derivatives in high yields. The mechanism and roles of the substrates were investigated and it was found that cyclic hydrazides were formed as intermediates.

Synthesis of indolin-2-one, isoindolin-1-one, and indole derivatives from homophthalic acid

We hereby report the preparation of indolin-2-one and isoindolin-1-one and their derivatives starting from 2-(carboxymethyl)benzoic acid, which was first regiospecifically converted into the isomeric half esters. Transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the regioisomeric isocyanates. Reaction of the isocyanates with aniline produced urethane derivatives. Intramolecular cyclization provided the target compounds. Georg Thieme Verlag Stuttgart. New York.

AMIDE DERIVATIVES

The invention concerns a compound of the Formula I (A chemical formula should be inserted here - please see paper copy enclosed herewith) wherein m is 0-2 and each R1 is a group such as hydroxy, halogeno, trifluoromethyl heterocyclyl and heterocyclyloxy; R2 is halogeno, trifluoromethyl or (1-6C)alkyl; R3 is hydrogen, halogeno or (1-6C)alkyl; and R4 is (3-6C)cycloalkyl;or pharmaceutically-acceptable salts thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical condions mediated by cytokines.