N bond cleavage
A catalyst-free, visible-light-induced annulation of 2H-azirines and hydrazonyl chlorides via EDA activation affords 1,3,5-triazines or imidazoles. The 2H-azirine substitution pattern controls reactivity, giving a practical route to N-heterocycles.
An unconventional route is proposed to achieve persistent 1H-azirine (usually unreachable at ambient conditions), from its more stable isomer 2H-azirine.
The Fe(II)-catalyzed cyclization of 2H-azirines and N,N-dimethylformamide as an amine source has been developed for the synthesis of 1-methyl-4,5-diaryl-1H-imidazoles.
A TfOH-catalysed ring opening of 2H-azirines by 2-mercaptopyridines and thiazole-2-thiols is reported to access imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles in one pot.
Two copper-controlled reactions of 2H-azirines with TosMICs have been developed that provide two efficient and modular approaches to diverse substituted pyrimidines with non-electron-withdrawing substituents at position 4 or 6.