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

Váňa, Lubomír; Jakubec, Martin; Sýkora, Jan; Císařová, I.; Storch, Jan; Církva, Vladimír

doi:https://dx.doi.org/10.1021/acs.joc.1c01113

Number of the records: 1

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

1.

SYSNO ASEP	0545651
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis of Aza[n]phenacenes (n = 4−6) via Photocyclodehydrochlorination of 2‑Chloro‑N‑aryl-1-naphthamides.
Author(s)	Váňa, Lubomír (UCHP-M) Jakubec, Martin (UCHP-M)_{RID, ORCID, SAI} Sýkora, Jan (UCHP-M)_{RID, ORCID, SAI} Císařová, I. (CZ) Storch, Jan (UCHP-M)_{RID, ORCID, SAI} Církva, Vladimír (UCHP-M)_{RID, ORCID, SAI}
Source Title	Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263 Roč. 86, č. 19 (2021), s. 13252-13264
Number of pages	13 s.
Language	eng - English
Country	US - United States
Keywords	copper-catalyzed synthesis ; phenanthridine derivatives ; photocyclization
Subject RIV	CC - Organic Chemistry
OECD category	Organic chemistry
R&D Projects	GA17-02578S GA ČR - Czech Science Foundation (CSF)
Method of publishing	Open access with time embargo (02.10.2022)
Institutional support	UCHP-M - RVO:67985858
UT WOS	000704707200007
EID SCOPUS	85115911804
DOI	10.1021/acs.joc.1c01113
Annotation	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
Workplace	Institute of Chemical Process Fundamentals
Contact	Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227
Year of Publishing	2022
Electronic address	http://hdl.handle.net/11104/0322685

Number of the records: 1