ABSTRACT
An efficient chromoselective photochemical process is presented for the synthesis of 2H-azirines and 1,3-diazabicylo[3.1.0]hex-3-enes from readily available vinyl azides. The method exploits continuous flow photochemistry to enable the safe consumption of the hazardous azide group and provides uniform irradiation using high-power LEDs at 365-450â nm. Additionally, a scaled telescoped process has been developed providing access to drug-like 1,6-dihydropyrimidines and pyrimidines via integrated ring-expansion and oxidation reactions. Given the prevalence of various azacyclic targets in pharmaceutical, agrochemical and materials applications it is anticipated that this methodology will enable further exploitations of these important scaffolds.
ABSTRACT
The application of a dual reactor coil for consecutive photochemical reactions is presented in continuous flow mode. This strategy enables for the first time the use of a single LED-based light source to perform two distinct photochemical reactions in an uninterrupted fashion. This approach is demonstrated for the telescoped synthesis and functionalisation of drug-like quinolines and compared to alternatives exploiting two photochemical reactor set-ups operated in sequence. The presented strategy enables the intensified exploitation of photochemical reactions in modern synthesis.