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

被引：9

作者：

Vana, Lubomir ^{[1
]}

Jakubec, Martin ^{[1
]}

Sykora, Jan ^{[3
]}

Cisarova, Ivana ^{[2
]}

Storch, Jan ^{[1
]}

Cirkva, Vladimir ^{[1
]}

机构：

[1] Czech Acad Sci, Dept Adv Mat & Organ Synth, Inst Chem Proc Fundamentals, Prague 16502 6, Czech Republic

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Prague 12840 2, Czech Republic

[3] Czech Acad Sci, Dept Analyt Chem, Inst Chem Proc Fundamentals, Prague 16502 6, Czech Republic

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 19期

关键词：

COPPER-CATALYZED SYNTHESIS; PHENANTHRIDINE DERIVATIVES; PHOTOCYCLIZATION; SUBSTITUTION; CYCLIZATION; PHENACENES; ACCEPTOR; ANALOGS;

D O I：

10.1021/acs.joc.1c01113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology for the synthesis of aza[n]-phenacenes was successfully developed utilizing photocyclodehydro-chlorination 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.

引用

页码：13252 / 13264

页数：13

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