3453-60-9

Usage

InChI:InChI=1/C11H10O4/c1-14-10(12)6-9-7-4-2-3-5-8(7)11(13)15-9/h2-5,9H,6H2,1H3

Upstream product

• 67-56-1 methanol 
• 612-40-8 2-carboxycinnamic acid 
• 292638-85-8 acrylic acid methyl ester 
• 65-85-0 benzoic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 1376293-20-7 methyl 2-(4-oxo-3-phenyl-3,4-dihydro-1H-2,3-benzoxazin-1-yl)acetate 
• 132316-45-1 methyl 2-formylcinnamate 
• 52753-91-0 (E)-methyl 3-(2-formylphenyl)acrylate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1079-02-3 benzoic acid-2,3,4,5,6-d5 
• 14783-89-2 ortho-carboxybenzenediazonium tetrafluoroborate 
• 4743-58-2 (3-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid 
• 102540-15-8 methyl (2E)-3-(2-bromophenyl)-2-propenoate 
• 77-78-1 dimethyl sulfate 

Relevant academic research and scientific papers

RhIII-Catalyzed C-H Olefination of Benzoic Acids under Mild Conditions using Oxygen as the Sole Oxidant

Phthalide skeletons have been synthesized for the first time through a RhIII-catalyzed C-H olefination of benzoic acids under mild conditions using oxygen as the sole oxidant. Aromatic acids bearing a variety of functional groups could react wi

RhIII-Catalyzed Regioselective Synthesis of Phthalides with Water as the Solvent

Under rhodium(III)-catalyzed conditions, a broad range of benzoic acids reacted with acrylates successfully to provide phthalides through the direct functionalization of a C–H bond followed by β-hydride elimination and intramolecular Michael addition. The reaction provides an alternative strategy for the construction of diverse and useful phthalide derivatives from readily available starting materials. In most cases, high regioselectivity was obtained, and this is the first report of the rhodium-catalyzed synthesis of phthalides in water.

NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides

An efficient NHC-catalyzed domino oxidation/oxa-Michael addition reaction of 2-alkenylbenzaldehydes has been developed to afford 3-substituted phthalides bearing a C3-stereogenic center with a broad substrate scope and wide functional group tolerance. The preliminary results of the asymmetric process have been provided as well. the Partner Organisations 2014.

N-heterocyclic carbene-catalyzed cascade annulation reaction of o-vinylarylaldehydes with nitrosoarenes: One-step assembly of functionalized 2,3-benzoxazin-4-ones

The NHC-catalyzed reactions of ortho electron-deficient vinyl substituted arylaldehydes with nitrosoarenes were studied. The reactions produced multifunctional 2,3-benzoxazin-4-ones in good to excellent yields via a cascade aza-benzoin reaction between aldehyde and nitroso groups followed by an intramolecular oxo-Michael addition. The resulting 1-acetate substituted 2,3-benzoxazinones were transformed into a new type of β-hydroxycarboxylate derivatives or 3-oxo-1-isobenzofuranacetates, respectively, under different reductive conditions. This work not only provides a simple and efficient method for the construction of multifunctional 2,3-benzoxazin-4-ones of potential pharmacological interest, but also expands the application of NHC-catalyzed cascade reactions in the formation of carbon-heteroatom and heteroatom- heteroatom bonds.

Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck-Matsuda reaction

Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone,

Microwave-enhanced carbonylative generation of indanones and 3-acylaminoindanones

(Chemical Equation Presented). The development of microwave-accelerated protocols for palladium(0)-catalyzed carbonylative cyclization of unsaturated aryl bromides and chlorides is described. By employing o-bromostyryl derivatives lacking substituents on the vinylic bond, molybdenum hexacarbonyl-mediated in situ carbonylation delivered a set of indan-1-one products in high yield after only 20 min of heating. Without the addition of the tri-tert-butylphosphine releasing Fu-salt ((t-Bu)3PHBF4), only incomplete conversions of sluggish o-styryl bromides and chlorides were realized. Internal and chemoselective palladium(0)-catalyzed Heck arylations of enamides afforded suitable starting materials for subsequent rapid ring-closing reactions. Microwave-heated intramolecular in situ carbonylation of these electron-rich and sterically congested olefins conveniently afforded eight functionalized 3-acylaminoindanone derivatives in a novel synthetic process. Attempted carbonylative annulation of electron-poor o-bromocinnamic acid derivatives furnished only the corresponding lactones via a competing hydroxycarbonylation- Michael addition reaction sequence.

Heterocyclic compounds for the treatment of CNS and cardiovascular disorders

Novel aromatic bicyclic amines of formula (I) STR1 are useful in treating central nervous system disorders and cardiac arrhythmias and cardiac fibrillation.

Formation of Lactones in the Heck Reaction

The Heck reaction of methyl 2-bromobenzoate with methyl acrylate gave a mixture of alkene 1 and lactone 9.Acrylonitrile and methyl 2-bromobenzoate gave lactone 10.Ethyl 2-bromobenzoate and methyl acrylate or acrylonitrile gave the alkenes 2 and 4 respecti

SYNTHESIS OF ISOCOUMARINS VIA THALLATION-OLEFINATION OF BENZOIC ACIDS

Benzoic acid and substituted benzoic acids are readily thallated by thallium(III) trifluoroacetate and subsequently reacted with palladium chloride and simple olefins, allylic halides, vinyl halides, or vinyl esters to give isocoumarins.The organic halide reactions are catalytic in palladium. 1,2- and 1,3-dienes also react catalytically to afford 4-alkylidene- and 3-vinyl-3,4-dihydroisocoumarins, respectively.Vinylcyclopropanes also afford 3-vinyl-3,4-dihydroisocoumarins.This highly convenient thallation-olefination approach appears quite general for the synthesis of isocoumarins.