Continuous flow synthesis of phenyl glucosazone and its conversion to 2H-1,2,3-Triazole building blocks

A continuous flow approach for the generation of phenyl glucosazone from glucose and phenyl hydrazine is reported giving the pure target in 53% isolated yield. This thermal process generates the target product as an insoluble material that causes reactor fouling via adhering to the reactor walls. To overcome this issue a segmented flow approach was realised whereby streams of air and the reaction solution were combined in a T-piece and directed through the heated reactor coil. The resulting micro-mixing prevented reactor fouling and blocking and allowed for multi-hour reactions to generate the desired target in high yield. The value of the phenyl glucosazone product was demonstrated via its oxidative cyclisation into 2H-phenyl-1,2,3-triazoles which represent important heterocyclic scaffolds.

Automated summary

A continuous flow approach was used to generate phenyl glucosazone from glucose and phenyl hydrazine, resulting in a 53% isolated yield of pure product. To overcome reactor fouling caused by the insoluble nature of the target product, a segmented flow approach was implemented, allowing for multi-hour reactions to generate high yield. The value of the phenyl glucosazone product was demonstrated through its conversion into important heterocyclic scaffolds.