3334-93-8

Upstream product

• 38560-27-9 N-(4-methylphenyl)azetidin-2-one 
• 2393-23-9 4-methoxy-benzylamine 
• 106-49-0 p-toluidine 
• 504-63-2 trimethyleneglycol 
• 5469-66-9 propane-1,3-diol ditosylate 

Relevant academic research and scientific papers

Synthesis of 2-Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4-Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy

Covalent attachment of a 1,2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited high catalytic activity in the preparation of 2-aryl isoindoline derivatives and symmetrical secondary amines. The catalyst system is highly recyclable for at least five times. Besides the important effect of the triazole, iridium sites grafted on siliceous supports can act as multifunctional catalytic centers and thus greatly enhance the catalytic activity of the catalysts. Furthermore, mechanistic experiments revealed that the reaction is initiated by an initial alcohol dehydrogenation and promoted by an iridium hydride intermediate. Importantly, the direct detection of a diagnostic iridium hydride signal confirmed that the synthesis of 2-aryl isoindolines occurs by a borrowing hydrogen process. This work provides an efficient example of isoindolines synthesis through a borrowing hydrogen strategy.

Utilization of Cyclic Amides as Masked Aldehyde Equivalents in Reductive Amination Reactions

An operationally simple protocol has been discovered that couples primary or secondary amines with N-aryl-substituted lactams to deliver differentiated diamines in moderate to high yields. The process allows for the partial reduction of a lactam in the presence of Cp2ZrHCl (Schwartz's reagent), followed by a reductive amination between the resulting hemiaminal and primary or secondary amine. These reactions can be telescoped in a one-pot fashion to significantly simplify the operation. The scope of amines and substituted lactams of various ring sizes was demonstrated through the formation of a range of differentiated diamine products. Furthermore, this methodology was expanded to include N-aryl pyrrolidinone substrates with an enantiopure ester group at the 5-position, and α-amino piperidinones were prepared with complete retention of stereochemical information. The development of this chemistry has enabled the consideration of lactams as useful synthons.

USE OF HEXAMETHYLPHOSPHORAMIDE (HMPA) IN THE ALKYLATION OF AROMATIC AMINES: SYNTHESIS OF AZETIDINES, PYRROLIDINES, PIPERIDINES AND HEXAHYDROAZEPINES

The direct alkylation of p-toluidine, as a model of aromatic amines, with 1,3-, 1,4-, 1,5- and 1,6-ditosylates, -dibromides or -dimesitylates in HMPA as solvent affords the corresponding cyclic amines.The convenience of this reaction and some observed lim