75519-84-5

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 70-11-1 α-bromoacetophenone 
• 70008-80-9 3-morpholin-4-yl-1-phenyl-but-2-en-1-one 
• 6832-16-2 methyl diazoacetate 
• 75-11-6 diiodomethane 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 108-24-7 acetic anhydride 
• 100-42-5 styrene 
• 637-44-5 phenylpropyolic acid 

Downstream Products

• 583-05-1 1-phenylpentane-1,4-dione 
• 28168-20-9 2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Tandem homologation-acylation chemistry: Single and double homologation

Treatment of β-dicarbonyls with the Furakawa-variant of the Simmons-Smith reagent results in homologation and production of an intermediate zinc enolate. Treatment of the enolate with various acylating agents generate products with both γ-dicarbonyl funct

Enantioselective Synthesis of Nitrogen-Nitrogen Biaryl Atropisomers via Copper-Catalyzed Friedel-Crafts Alkylation Reaction

Nitrogen-nitrogen bonds containing motifs are ubiquitous in natural products and bioactive compounds. However, the atropisomerism arising from a restricted rotation around an N-N bond is largely overlooked. Here, we describe a method to access the first enantioselective synthesis of N-N biaryl atropisomers via a Cu-bisoxazoline-catalyzed Friedel-Crafts alkylation reaction. A wide range of axially chiral N-N bisazaheterocycle compounds were efficiently prepared in high yields with excellent enantioselectivities via desymmetrization and kinetic resolution. Heating experiments showed that the axially chiral bisazaheterocycle products have high rotational barriers.

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of ?-Diketones and ?-Ketonitriles

A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)-H bond functionalization to construct new C-C bonds and C-O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to ?-diketones and ?-ketonitriles. A possible mechanism is proposed.

Highly atroposelective synthesis of arylpyrroles by catalytic asymmetric Paal-Knorr reaction

A general and efficient method for accessing enantiomerically pure arylpyrroles by utilizing the catalytic asymmetric Paal-Knorr reaction has been developed for the first time. A wide range of axially chiral arylpyrroles were obtained in high yields with

Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones

A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp3)-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.

Cerium-catalyzed, aerobic oxidative synthesis of 1,2-dioxane derivatives from styrene and their fragmentation into 1,4-dicarbonyl compounds

1,4-Diketones were prepared by cerium-catalyzed oxidative coupling of styrene with molecular oxygen and 1,3-dicarbonyl compounds. This two-step sequence was performed as a one-pot procedure without isolation of the intermediate products. The first step is

Formation of 1,4-diketones by aerobic oxidative C-C coupling of styrene with 1,3-dicarbonyl compounds

(Chemical equation presented). Convenient and direct: 1,4-Dicarbonyl compounds are readily obtained through a one-pot cerium-catalyzed oxidative C-C coupling in the presence of oxygen and subsequent fragmentation. The products are suitable precursors for

Alkoxycarbonylcarbene Transfer to Acyclic Tertiary Enaminones

Copper-catalyzed alkoxycarbonylcarbene transfer from methyl or tert-butyl diazoacetate to acyclic enaminoesters 6a,b and enaminocarboxanilide 13 yields vicinal push-pull-substituted cyclopropanes 7a,b, 8, and 14. In contact with dry silica gel, the latter compounds undergo facile ring-opening leading to enaminoesters 9,10, and 15. Treatment with aqueous acid transforms 9 and 10 into 2-acylsuccinates 11 and 12, and 15 into pyrrolinone 16. Methoxycarbonylcarbene transfer to enaminoketones 1a-c does not yield isolable cyclopropanes, but after hydrolytic work-up α-acyl-γ-ketoesters 2a-c are obtained.

THERAPEUTIC AGENT FOR DIABETES

A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.