Synthesis of Aza[n]phenacenes (n = 4−6) via Photocyclodehydrochlorination of 2‑Chloro‑N‑aryl-1-naphthamides.

0545651 - ÚCHP 2022 RIV US eng J - Journal Article
Váňa, Lubomír - Jakubec, Martin - Sýkora, Jan - Císařová, I. - Storch, Jan - Církva, Vladimír
Synthesis of Aza[n]phenacenes (n = 4−6) via Photocyclodehydrochlorination of 2‑Chloro‑N‑aryl-1-naphthamides.
Journal of Organic Chemistry. Roč. 86, č. 19 (2021), s. 13252-13264. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR(CZ) GA17-02578S
Grant - others:AV ČR(CZ) StrategieAV21/3
Program: StrategieAV
Institutional support: RVO:67985858
Keywords : copper-catalyzed synthesis * phenanthridine derivatives * photocyclization
OECD category: Organic chemistry
Impact factor: 4.198, year: 2021
Method of publishing: Open access with time embargo

A novel methodology for the synthesis of aza[n]-phenacenes was successfully developed utilizing photocyclodehydrochlorination reaction of 2-chloro-N-aryl-1-naphthamides. In these key intermediates, the factors influencing the photoreaction were studied. The target aza[n]phenacenes were obtained by triflation or chlorination from prepared phenanthridinones, followed by hydrogenation. The introduction of a nitrogen atom into a phenacene skeleton induced changes in the physicochemical properties. The important properties of prepared aza[n]phenacenes (n = 4−6) were studied experimentally and by density functional theory calculations and were compared to those of
their carbo analogues. Furthermore, some important features of the crystalline aza[n]phenacenes were investigated, including intermolecular interaction in the crystal lattice and the increased solubility or decreased melting points
Permanent Link: http://hdl.handle.net/11104/0322685