Naslov
Synthesis and Structural Elucidation of Diversely Functionalized 5, 10-Diaza[5]Helicenes

Autori
Waghray, Deepali ; Zhang, Jing ; Jacobs, Jeroen ; Nulens, Wienand ; Basarić, Nikola ; Van Meervelt, Luc ; Dehaen, Wim

Izvornik
Journal of organic chemistry (0022-3263) 77 (2012), 22; 10176-10183

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
diaza[5]helicenes; Wittig reaction; photochemical electrocyclization

Sažetak
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 methoxysubstituted diaza[5]helicenes. A resolution strategy based on diastereomeric separation by substitution of the dichloro derivative with a chiral amine has been shown.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA