166263-27-0

Upstream product

• 75-30-9 2-iodo-propane 
• 97-51-8 5-Nitrosalicylaldehyde 
• 75-26-3 isopropyl bromide 
• 100-02-7 4-nitro-phenol 
• 22921-58-0 2-isopropoxybenzaldehyde 
• 90-02-8 salicylaldehyde 

Downstream Products

• 502848-71-7 1-isopropoxy-4-nitro-2-vinylbenzene 
• 778649-56-2 1-isopropoxy-4-nitro-2-(prop-1-en-1-yl)benzene 
• 948992-36-7 2-(azidomethyl)-1-isopropoxy-4-nitrobenzene 
• 948992-35-6 (2-isopropoxy-5-nitrophenyl)methanol 

Relevant academic research and scientific papers

Nitration under continuous flow conditions: Convenient synthesis of 2-isopropoxy-5-nitrobenzaldehyde, an important building block in the preparation of nitro-substituted Hoveyda-Grubbs metathesis catalyst

Herein, we describe the use of continuous flow chemistry for selective, efficient and reproducible nitration of 2-isopropoxybenzaldehyde to produce the desired 2-isopropoxy-5-nitrobenzaldehyde, an important building block in the preparation of a ligand of nitro-substituted Hoveyda-Grubbs metathesis catalyst. Nitration was done with red fuming HNO3, and this challenging and hazardous process was performed using a flow-through silicon-glass microreactor equipped with a set of temperature sensors, and with a productivity of 13 g/h, providing us with a reproducible chemical process amenable for production of sufficient quantities of 2-isopropoxy-5-nitrobenzaldehyde for ongoing large-scale synthesis of nitro-substituted Hoveyda-Grubbs metathesis catalyst.

Ruthenabenzene: A Robust Precatalyst

Metallaaromatics constitute a unique class of aromatic compounds where one or more transition metal elements are incorporated into the aromatic system, the parent of which is metallabenzene. One of the main concerns about metallabenzenes generally deals with the structural characterization related to their relative aromaticity compared to the carbon archetype. Transition metal-containing metallabenzenes are also implicated in certain catalytic processes such as alkyne metathesis polymerization; however, these transition metal-based metallaaromatic compounds have not been developed as a catalyst. Herein, we describe an effective strategy to generate diverse arrays of ruthenabenzenes and demonstrated them as an aromatic equivalent of the Grubbs-type ruthenium alkylidene catalysts. These ruthenabenzenes can be prepared via an enyne metathesis and metallotropic [1,3]-shift cascade process to form alkyne-chelated ruthenium alkylidene intermediates followed by spontaneous cycloaromatization. The aromatic nature of these complexes was confirmed by spectroscopic and X-ray crystallographic data, and the mechanistic pathways for the cycloaromatization process were studied by DFT calculations. These ruthenabenzenes display robust catalytic activity for metathesis and other transformations, which illustrates that metallabenzenes are not only compounds of structural and theoretical interests but also are a novel platform for new catalyst development.

Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

A series of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acids/carbohydrazides as analogues of febuxostat were synthesized and evaluated for their in vitro xanthine oxidase (XO) inhibitory activity. Among these compounds, the carboxylic acid derivatives 7a-h and 8a-h exhibited high potency in the submicromolar/nanomolar range. Steady-state kinetics experiment revealed that 7f was a mixed-type inhibitor of xanthine oxidase. In addition, a molecular docking study of 7f was performed to determine its binding mode at the active site of xanthine oxidase.

Remarkable Ability of the Benzylidene Ligand To Control Initiation of Hoveyda–Grubbs Metathesis Catalysts

The structure of the chelating benzylidene ligand offers the unique ability to control the initiation of Hoveyda–Grubbs metathesis catalysts. Apart from steric and electronic effects acting on the step involving opening of the chelate ring, changes related to the following ligand-exchange process may also play a critical role. Our mechanistic model reveals that ligands substituted at the 6-position of the benzylidene ring enter the metathesis cycle in a nonoptimal chelating conformation, and thus the coordination number of the ruthenium center transiently increases to six (associative mechanism). In effect, the synthesis and initiation of the catalysts becomes difficult, and the energy barrier of the ligand-exchange process is controlled by the structure of the coordinating OR group. Moreover, we explain how isomeric naphthalene ligands affect the catalytic performance by an indivisible combination of steric and π-electron delocalization effects.

Phosphinate ruthenium complexes

Provided herein are ruthenium complexes of Formula I, and processes of preparation thereof. Also provided are methods of their use as a metathesis catalyst.

2-(ARYLOXY)ACETAMIDE FACTOR VIIA INHIBITORS USEFUL AS ANTICOAGULANTS

The present invention relates generally to novel 2-(aryloxy)acetamides of Formula (I) or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates, or prodrugs thereof, wherein the variables W, Y, Z, R7, R8, and R9 are as defined herein. These compounds are selective inhibitors of the serine protease coagulation factor VIIa which can be used as medicaments.

Recyclable ruthenium catalysts for metathesis reactions

The invention relates to novel carbene ligands and their incorporated monomeric and resin/polymer linked ruthenium catalysts, which are recyclable and highly active for olefin metathesis reactions. It is disclosed that significant electronic effect of different substituted 2-alkoxybenzylidene ligands on the catalytic activity and stability of corresponding carbene ruthenium complexes, some of novel ruthenium complexes in the invention can be broadly used as catalysts highly efficient for olefin metathesis reactions, particularly in ring-closing (RCM), ring-opening (ROM), ring-opening metathesis polymerization (ROMP) and cross metathesis (CM) in high yield. The invention also relates to preparation of new ruthenium complexes and the use in metathesis.

RUTHENIUM COMPLEXES AS (PRE)CATALYSTS FOR METATHESIS REACTIONS

The invention relates to new (pre)catalysts of ruthenium complexes of formula (I), wherein L1, X, X', R1, R2, R3 and n are defined herein. The novel ruthenium complexes of formula 1 are convenient (pre)catalysts

Nitro-substituted Hoveyda-Grubbs ruthenium carbenes: Enhancement of catalyst activity through electronic activation

The design, synthesis, stability, and catalytic activity of nitro-substituted Hoveyda-Grubbs metathesis catalysts are described. The highly active and stable meta- and para-substituted complexes are attractive from a practical point of view. These catalys

Ruthenium complexes as (pre)catalysts for metathesis reactions

The invention relates to new (pre)catalysts of ruthenium complexes of formula 1, 1 wherein L1, X, X′, R1, R2, R3 and n are defined herein. The novel ruthenium complexes of formula 1 are convenient (pre)catalysts for metathesis reactions and can be applied, e.g., for ring-closing metathesis, cross metathesis or ene-ine metathesis reactions. Another aspect of the invention are the novel intermediates of formula 2. 2