55810-22-5Relevant academic research and scientific papers
Visible-Light Photoredox Catalyzed Double C-H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides
Jiang, Si,Tian, Xiao-Jing,Feng, Shu-Yao,Li, Jiang-Sheng,Li, Zhi-Wei,Lu, Cui-Hong,Li, Chao-Jun,Liu, Wei-Dong
, p. 692 - 696 (2021/02/01)
A visible-light photoredox catalyzed radical cascade cyclization of simple ethers with cyanamides is developed at room temperature. This strategy involves sequential inert Csp3-H/Csp2-H functionalizations through intermolecular addition reaction of oxyalkyl radicals to N-cyano groups followed by radical cyclization of iminyl radicals in situ generated with C-2 aryl rings. This method allows for efficient synthesis of tetracyclic benzo[4,5]imidazo[1,2-c]quinazolines. Importantly, this is the first example of an intermolecular-intramolecular radical cascade cyclization reaction of cyanamides.
Photochemical arylation of Bronsted acids with 2-azidobenzimidazole
Sudakow, Alex,Jones, Peter G.,Lindel, Thomas
supporting information; experimental part, p. 681 - 684 (2012/03/11)
Irradiation of N-benzylated 2-azidobenzimidazoles at 300 nm in the presence of an excess amount of carboxylic acids results in a novel regioselective synthesis of 2-amino-6-oxybenzimidazoles in isolated yields of 60-70 %. It is also possible to regioselectively introduce 6-bromo, 6-chloro, and 6-triflyloxy groups. Irradiation in dichloromethane in the absence of external nucleophiles revealed that after loss of nitrogen, the benzimidazolylnitrene probably undergoes coarctate ring opening to an N-cyano diaza-o-xylylene intermediate. Photolysis of 2-azidobenzimidazoles in the presence of carboxylic or sulfonic acidsleads to regioselective oxygenation of the 6-position in good yield. Copyright
2-quinoxalinylnitrenes and 4-quinazolinylnitrenes: Rearrangement to cyclic and acyclic carbodiimides and ring-opening to nitrile ylides
Kvaskoff, David,Vosswinkel, Michael,Wentrup, Curt
scheme or table, p. 5413 - 5424 (2011/06/21)
This work was undertaken with the aim to obtain direct evidence for the interrelationships between hetarylnitrenes, their ring-expanded cyclic carbodiimide isomers, and ring-opened nitrile ylides. Tetrazolo[1,5-a] quinoxaline 11T and tetrazolo[5.1-c]quina
THERMOLYSIS OF 4-AZIDOPYRIMIDINES AND 4-AZIDOQUINAZOLINES
Giammanco, Lorenzo,Invidiata, Francesco Paolo
, p. 1459 - 1464 (2007/10/02)
A facile thermolysis of 4-azidopyrimidines and 4-azidoquinazolines leading, by ring contraction, in excellent yields to 1-cyanoimidazoles and benzimidazoles is reported.
