16418-23-8

Upstream product

• 5227-55-4 2,3-diphenyl quinoxaline N-oxide 
• 95-54-5 1,2-diamino-benzene 
• 98-88-4 benzoyl chloride 
• 744-38-7 1,2-dibenzamidobenzene 

Relevant academic research and scientific papers

Scaffold hopping by net photochemical carbon deletion of azaarenes

Discovery chemists routinely identify purpose-tailored molecules through an iterative structural optimization approach, but the preparation of each successive candidate in a compound series can rarely be conducted in a manner matching their thought process. This is because many of the necessary chemical transformations required to modify compound cores in a straightforward fashion are not applicable in complex contexts. We report a method that addresses one facet of this problem by allowing chemists to hop directly between chemically distinct heteroaromatic scaffolds. Specifically, we show that selective photolysis of quinoline N-oxides with 390-nanometer light followed by acid-promoted rearrangement affords N-acylindoles while showing broad compatibility with medicinally relevant functionality. Applications to late-stage skeletal modification of compounds of pharmaceutical interest and more complex transformations involving serial single-atom changes are demonstrated.

BF3·Et2O promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines

2-Substituted benzimidazoles and 3,1,5-benzoxadiazepines have been synthesized in excellent yields in a single pot by cyclodehydration of N-acyl-1,2-phenylenediamines and N,N′-diacyl-1,2- phenylenediamines prepared in situ from the corresponding 1,2-phenylenediamines and an acid chloride, respectively.

Novel Synthesis and Rearrangement of 3,1,5-Benzoxadiazepines

N,N'-Diacyl-o-phenylenediamines react with dibromotriphenylphosphorane in the presence of triethylamine as HBr captor to give 3,1,5-benzoxadiazepines in good yields.If the reaction is carried out without acid acceptor the initially formed 3,1,5-benzoxadia