13170-61-1

Upstream product

• 60-29-7 diethyl ether 
• 63378-87-0 1,2-diphenylhexahydropyridazine 
• 7647-01-0 hydrogenchloride 
• 71-43-2 benzene 
• 123-75-1 pyrrolidine 
• 62-53-3 aniline 
• 3422-01-3 tert-butyl phenylcarbamate 
• 110-56-5 1,4-dichlorobutane 
• 110-52-1 1,4-dibromo-butane 
• 108-90-7 chlorobenzene 
• 223394-90-9 N-phenyl-tetramethylenediamine 
• 124119-54-6 N,N'-butanediyl-bis-toluene-4-sulfonanilide 

Downstream Products

• 20972-43-4 trans-azoxybenzene 
• 63378-87-0 1,2-diphenylhexahydropyridazine 

Relevant academic research and scientific papers

Synergetic activation of CO2by the DBU-organocatalyst and amine substrates towards stable carbamate salts for synthesis of oxazolidinones

The development of an efficient methodology to transform CO2 into valuable chemicals has attracted increasing attention concerning the challenging issues of CO2-utilization. Herein, an efficient approach for the preparation of oxazolidinones from CO2, primary (aliphatic/aromatic) amines and 1,2-dichloroethane (or its derivatives) catalyzed by DBU organo-superbase was achieved with yields of 47-97% under mild conditions (80-100 °C, 12 h, 1.0 MPa CO2). Control experiments demonstrated that the formation of an ion-pair carbamate salt intermediate IS-B derived from the reaction of CO2, DBU (catalyst) and an amine (substrate) was the key step for this three-component reaction. The available DBU-amine-CO2 adduct intermediate (like IS-B-2) with fair stability will evolve into the thermodynamically stable product oxazolidinones upon attack of 1,2-dichloroethane (or its derivatives), along with the regeneration of the DBU catalyst. Alternatively, the decomposition of the DBU-aryl amine-CO2 adduct (like IS-B-1) with relatively poor stability also could result in the competitive substitution reaction of 1,2-dichloroethane (or its derivatives) with the aryl amine. This work provides insights into synergetic CO2-activation by the DBU-catalyst and a nucleophilic amine-substrate via the formation of robust carbamate salt intermediates responsible for the final production of oxazolidinones. This journal is

Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene

Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several "azoxyarene analogues" of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.

Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors

In order to identify novel anti-hepatitis C virus (HCV) agents we devised cell-based strategies and screened phenotypically small molecule chemical libraries with infectious HCV particles, and identified a hit compound (1) containing a hexahydropyrimidine (HHP) core. During our cell-based SAR study, we observed a conversion of HHP 1 into a linear diamine (6), which is the active component in inhibiting HCV and exhibited comparable antiviral activity to the cyclic HHP 1. In addition, we engaged into the biological characterization of HHP and demonstrated that HHP does not interfere with HCV RNA replication, but with entry and release of viral particles. Here we report the results of the preliminary SAR and mechanism of action studies with HHP.

LIGANDS FOR TRANSITION-METAL-CATALYZED CROSS-COUPLINGS, AND METHODS OF USE THEREOF

Ligands for transition metals are disclosed herein, which may be used in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The disclosed methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition-metal-catalyzed cross-coupling reactions.

A highly active catalyst for Pd-catalyzed amination reactions: Cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides

A catalyst system based on a new biarylmonophosphine ligand (BrettPhos) that shows excellent reactivity for C-N cross-coupling reactions is reported. This catalyst system enables the use of aryl mesylates as a coupling partner in C-N bond-forming reactions. Additionally, the use of BrettPhos permits the highly selective monoarylation of an array of primary aliphatic amines and anilines at low catalyst loadings and with fast reaction times, including the first monoarylation of methylamine. Lastly, oxidative addition complexes of BrettPhos are included, which provide insight into the origin of reactivity for this system. Copyright

A novel salt-free ruthenium-catalyzed alkylation of aryl amines

The alkylation of aryl amines using cyclic amines such as pyrrolidine proceeds via borrowing hydrogen methodology in the presence of 1 mol % Shvo catalyst. During the reaction multiple carbon-nitrogen cleavage and formation occurred. This novel reaction sequence leads to N-aryl-pyrrolidines and -piperidines.