5186-54-9

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 7782-77-6 cis-nitrous acid 
• 941-55-9 4-toluenesulfonyl azide 
• 4438-85-1 3H-chromene-2,4-dione 
• 75020-20-1 9-Oxo-1H,9H-benzopyrano<2,3-d>-v-triazole 
• 5725-79-1 3-amino-4-hydroxy-2H-chromen-2-one 

Downstream Products

• 109797-45-7 3-[2'-cyclohexenyl]-4-hydroxy-1-benzopyran-2(H)-one 
• 94302-75-7 4-(4-methoxyphenyl)-4-hydroxycoumarin 
• 6619-24-5 4-hydroxy-3-<(4-methylphenyl)methyl>-2H-1-benzopyran-2-one 
• 73791-11-4 3-<2,5-Dimethyl-phenyl>-4-hydroxy-cumarin 
• 15074-18-7 3-benzyl-4-hydroxycoumarin 
• 73791-18-1 4-hydroxy-3-o-tolyl-chromen-2-one 
• 73791-19-2 4-hydroxy-3-(p-tolyl)-1-benzopyran-2-one 
• 1786-05-6 4-hydroxy-3-phenylcoumarin 

Relevant academic research and scientific papers

Polyoxygenated coumarins. Oxonium ylides en route to polyoxa- macrocyclic coumarins

The overall sequence of Rh(II)-catalysed carbenoid generation, oxonium ylide formation and subsequent sigmatropic rearrangement utilising 3-diazo- 2H-1-benzopyran-2,4(3H)-dione in cyclic ethers as solvents has been satisfactorily used to achieve the synthesis of several medium- to large- membered polyoxa macrocycles embodying the coumarin subunit.

A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis

Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.

Dichlorination of α-Diazo-β-dicarbonyls using (dichloroiodo)benzene

Abstract α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleo-philicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.

Direct ionic liquid promoted organocatalyzed diazo-transfer reactions: diversity-oriented synthesis of diazo-compounds

A practical and novel ionic liquid promoted organocatalytic selective diazo-transfer process for the synthesis of highly substituted diazo-compounds in high yields is reported. The ionic liquid can be reused without affecting the reaction rates or yields over five runs.

Photoactive coumarin sulfonate compounds

A new class of 3-diazo-3,4-dihydrocoumarin compounds which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include 6-sulfonyl-3-diazo-4-oxo-3,4-dihydrocoumarin esters. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Process for preparing coumarin sulfonates

A novel process for preparing sulfonic acid esters and amides of benzo-heterocyclic diazo diketo compounds, such as substituted diazo-4-oxo-3,4-dihydrocoumarins, which are useful synthetic intermediates in a wide variety of applications including photoresists, opto-electronics, agricultural, and pharmaceutical applications is disclosed and claimed. The process comprises the steps of (a) subjecting a substituted benzo-heterocyclic β-keto-enol compound to suitable diazo transfer conditions in the presence of a diazo transfer agent; (b) subjecting the so formed diazo diketo compound to suitable halosulfonation conditions in the presence of a halosulfonation agent; and (c) subjecting the so formed halosulfonyl aromatic compound to suitable substitution reaction in the presence of an alcohol or an amine to form the corresponding sulfonic acid ester or amide of benzo-heterocyclic diazo diketo compound. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.

Five- and Six-Membered Ring Reductones from 2-Diazo-1,3-dicarbonyl Compounds. A Smoothful Alternative of the Classic Thermal Dediazotation

2-Acyloxy-2-chloro-1,3-dicarbonyl compounds 2, easily obtained from 2-diazo-1,3-dicarbonyl compounds 1 and tert-butyl hypochlorite in formic or acetic acid at room temperature or below are immediately reduced to the corresponding reductone esters 3 by sod