1407185-49-2Relevant academic research and scientific papers
Synthesis and structural elucidation of diversely functionalized 5,10-diaza[5]helicenes
Waghray, Deepali,Zhang, Jing,Jacobs, Jeroen,Nulens, Wienand,Basaric, Nikola,Meervelt, Luc Van,Dehaen, Wim
, p. 10176 - 10183 (2013/01/15)
Diversely functionalized diaza[5]helicenes have been synthesized starting from 6,9-dichloro-5,10-diaza[5]helicene, which was prepared from a readily available quinoline building block via Wittig reaction followed by photochemical electrocyclization. The helicene skeleton was substituted by a variety of O-, S-, N-, and C-centered nucleophiles using nucleophilic aromatic substitution reactions and palladium-catalyzed reactions like Suzuki coupling and Buchwald-Hartwig aminations. We have determined, using X-ray single-crystal diffraction, the crystal structures of the chloro- and methoxy-substituted diaza[5]helicenes. A resolution strategy based on diastereomeric separation by substitution of the dichloro derivative with a chiral amine has been shown.
