91838-74-3

Upstream product

• 77-78-1 dimethyl sulfate 
• 1448-87-9 2-chloroquinoxaline 
• 1104636-73-8 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 36856-91-4 2-bromo-quinoxaline 
• 7251-61-8 2-methylquinoxaline 
• 50-00-0 formaldehyd 
• 75927-49-0 pinacol vinylboronate 

Downstream Products

• 1210881-27-8 2-phenethylquinoxaline 
• 81516-60-1 2-(1-propyl)quinoxaline 

Relevant academic research and scientific papers

Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines**

We report a method for the synthesis of chiral vicinal chloroamines via asymmetric protonation of catalytically generated prochiral chloroenamines using chiral Br?nsted acids. The process is highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations. We show the utility of the method as an approach to the synthesis of a broad range of heterocycle-substituted aziridines by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines.

Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines

Cu-catalyzed three-component couplings of vinylazaarenes, B2(pin)2, and N-Boc imines are described. Oxidation of the initially formed boronate gives azaarene-containing, Boc-protected amino alcohols with reasonable to good diastereoselectivities.

Facile catalyst-free synthesis of 2-vinylquinolines via a direct deamination reaction occurring during Mannich synthesis

A facile catalyst-free method for the synthesis of 2-vinylquinolines via a direct deamination reaction during Mannich synthesis has been developed. Instantaneous hydrogen transfer via a six-membered ring intermediate is proposed as a key step for the direct deamination reaction. This reaction strategy tolerates a broad substrate scope and provides a highly efficient way to synthesize 2-vinylquinolines with adequate yields.

Enantioselective copper-catalyzed reductive coupling of alkenylazaarenes with ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of C=N-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection.

Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: Mechanisms correlated to charge distributions

The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges.

SLOW RELEASE OF ORGANOBORONIC ACIDS IN CROSS-COUPLING REACTIONS

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1-B-T; where R1 represents an organic group, T represents a conformationalIy rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a pal ladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

Piperazine derivatives for treatment of bacterial infections

Piperazine derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly in man.