Revisiting Hafner's Azapentalenes: The Chemistry of 1,3-Bis(dimethylamino)-2-azapentalene

被引：1

作者：

Meiszter, Eniko ^{[1
,2
]}

Gazdag, Tamas ^{[1
,3
]}

Mayer, Peter J. ^{[1
]}

Kunfi, Attila ^{[1
]}

Holczbauer, Tamas ^{[4
,5
]}

Sulyok-Eiler, Mate ^{[3
,6
]}

London, Gabor ^{[1
]}

机构：

[1] HUN REN Res Ctr Nat Sci, Inst Organ Chem, MTA TTK Lendulet Funct Organ Mat Res Grp, H-1117 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Fac Chem Technol & Biotechnol, Dept Organ Chem & Technol, H-1111 Budapest, Hungary

[3] Eotvos Lorand Univ, Hevesy Gyorgy PhD Sch Chem, H-1117 Budapest, Hungary

[4] HUN REN Res Ctr Nat Sci, Inst Organ Chem, Chem Crystallog Res Lab, H-1117 Budapest, Hungary

[5] HUN REN Res Ctr Nat Sci, Inst Organ Chem, Stereochem Res Grp, H-1117 Budapest, Hungary

[6] Eotvos Lorand Univ, Inst Chem, Lab Struct Chem & Biol, H-1117 Budapest, Hungary

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 09期

关键词：

ANTIAROMATICITY; DELOCALIZATION; IDENTIFICATION; AROMATICITY; PENTALENE; AZULENE; DESIGN;

D O I：

10.1021/acs.joc.3c02564

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stable azaheterocyclic derivatives of pentalene have been reported by the group of Hafner in the 1970s. However, these structures remained of low interest until recently, when they started to be investigated in the context of organic light-emitting diodes' (OLEDs') development. Herein, we revisit the synthesis of stable azapentalene derivative 1,3-bis(dimethylamino)-2-azapentalene and further explore its properties both computationally and experimentally. Beyond the reproduction and optimization of some previously reported transformations, such as formylation and amine substitution, the available scope of reactions was expanded with azo-coupling, selective halogenations, and cross-coupling reactions.

引用

页码：5941 / 5951

页数：11

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