80387-74-2

Upstream product

• 114097-28-8 N-(3,5-dimethylphenyl)-4-methyl-benzenesulfonamide 
• 77-78-1 dimethyl sulfate 
• 556-96-7 5-bromo-1,3-xylene 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 108-69-0 3,5-dimethylaminoaniline 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 80398-80-7 N-methyl N-(3,5-dimethylphenyl)hydrazine 
• 80387-67-3 2-methylindole-3-carboxaldehyde N,3,5-trimethylphenylhydrazone 
• 62959-13-1 N-nitroso-N,3,5-trimethylaniline 
• 13342-20-6 N-methyl-3,5-dimethylaniline 

Relevant academic research and scientific papers

Pd-catalyzed intermolecular amidation of aryl halides: The discovery that xantphos can be trans-chelating in a palladium complex

A general method for the intermolecular coupling of aryl halides and amides using a Xantphos/ Pd catalyst is described. This system displays good functional group compatibility, and the desired C-N bond forming process proceeds in good to excellent yields with 1-4 mol % of the Pd catalyst. Additionally, the arylation of sulfonamides, oxazolidinones, and ureas is reported. The efficiency of these transformations was found to be highly dependent on reaction concentrations and catalyst loadings. A Pd complex resulting from oxidative addition of 4-bromobenzonitrile, (Xantphos)Pd(4-cyanophenyl)(Br) (II), was prepared in one step from Xantphos, Pd2(dba)3, and the aryl bromide. Complex II proved to be an active catalyst for the coupling between 4-bromobenzonitrile and benzamide. X-ray crystallographic analysis of II revealed a rare trans-chelating bisphosphine-Pd(II) structure with a large bite angle of 150.7°.

New Rearrangements of Arylhydrazones in Polyphosphoric Acid: Extension to the Thiophene and Indole Series. 5

The behavior toward polyphosphoric acid of arylhydrazones of a few heterocyclic carbonyl compounds of the thiophene and indole series is described.The phenylhydrazone and 2,6-dimethylphenylhydrazone of ethyl α-thienylglyoxylate gave ethyl 4- and 5-(4-aminoaryl)-α-thienylglyoxylate, arising from two different sigmatropic rearrangements.The N,3,5-trimethylphenylhydrazone of 2-methylindole-3-carboxaldehyde afforded the 4--2-methylindole-3-carboxaldehyde resulting from a sigmatropic rearrangement, while the 2,6-dimethylphenylhydrazone of the same carbonyl compound unexpectedly gave the 3-(4-amino-3,5-dimethylphenyl)-2-methylindole-3-carboxaldehyde generated through a sigmatropic reaction.Chemical evidences are given for the assigned structures.