6375-27-5

Usage

Chemical Properties

White Crysstalline

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 644, 1946 DOI: 10.1021/ja01208a035

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 102-56-7 2,5-dimethoxyaniline 
• 141-97-9 ethyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 15925-47-0 S-tert-butyl acetothioacetate 
• 691-45-2 acetylketene 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 80357-46-6 1-(2,5-Dimethoxy-phenyl)-2,6-dimethyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (2,5-dimethoxy-phenyl)-amide 
• 23947-41-3 4-methyl-5,8dimethoxy-2(1H)-qunolinone 
• 66570-51-2 2,5,8-Trimethoxy-4-methyl-chinolin 
• 58868-27-2 2-chloro-5,8-dimethoxy-4-methylquinoline 
• 58868-16-9 N-(2,5-Dimethoxy-phenyl)-2-methyl-3-oxo-butyramide 
• 23947-41-3 5,8-Dimethoxy-4-methylcarbostyril 

Relevant academic research and scientific papers

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used to prepare novel Biginelli dihydropyrimidine derivatives. The introduction of the amino acid derivatives potentially allows for the exploration of new structural complexity and topologically diversifies the chemical space occupied by this versatile chemical scaffold.

1,2-Naphthoquinone-based Derivatives and and Methods for Preparing them

The present invention relates to a compound represented by chemical formula (1), a pharmaceutically acceptable salt, a hydrate, a solvate, a prodrug, a tautomer, an enantiomer, or a pharmaceutically acceptable diastereomer thereof, a preparing method thereof, and a medical composition having a treating or preventing effect of metabolic diseases containing the same. Here, R_1 to R_3, and X_1 to X_6 are the same as defined in a first claim.COPYRIGHT KIPO 2015

Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities

An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.

A general synthesis of quinoline-2,5,8(1H)-triones via acylation of 2,5- dimethoxyaniline with S-tert-butyl thioacetates by application of the Knorr cyclization

An efficient synthesis of quinoline-2,5,8(1H)-triones bearing alkyl groups at C3 and/or C4 is described. The reaction sequence employed involves Knorr cyclization of 2,5-dimethoxyanilides into 5,8- dimethoxyquinoline systems, followed by oxidative demethylation with cerium ammonium nitrate. The starting 2,5-dimethoxyanilides were prepared by chemoselective acylation of 2,5-dimethoxyaniline with a series of β-oxo thioesters obtained by regioselective alkylation of S-tert-butyl acetothioacetate (1) at C2 and/or C4. The introduction of electrophiles other than alkyl groups at C2 on 1 was also studied.

A comparative study of synthetic approach to 1-methyl-2,5,8(1H)-quinolinetrione and 4-methyl-2,5,8(1H)-quinolinetrione

The best overall yield for 1-methyl-2,5,8(1H)-quinolinetrione was obtained by the dichromate oxidation of 1-methyl-8-hydroxy-2-quinolone. 4-Methyl-2,5,8(1H)-quinolinetrione was synthesized by acetoacetylation of 2,5-dimethoxyaniline with 2,2,6-trimethyl-4H-1,3-dioxin-4-one followed by oxidation with ceric ammonium nitrate.