Synthesis and Properties of 5-Azaullazines

被引：6

作者：

Janke, Sophie ^{[1
]}

Boldt, Sebastian ^{[1
]}

Nakielski, Pascal ^{[1
]}

Villinger, Alexander ^{[1
]}

Ehlers, Peter ^{[1
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Catalysis LIKAT, D-18059 Rostock, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

关键词：

MEDIATED SYNTHESIS; ULLAZINE; ANNULATION; DESIGN; YIELD; DYES;

D O I：

10.1021/acs.joc.3c00386

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Azaullazines, indolizino[6,5,4,3-ija][1,5]naphthyridines,and their benzo-fused analogues were prepared in three steps by combinationof Pd catalyzed cross-coupling reactions with Bronsted acid mediatedcycloisomerisations. The reaction tolerates various substitution patternsand functional groups and proceeds in high yields. Optical and electrochemicalproperties of selected products were studied experimentally and byDFT calculations.

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收藏

页码：10470 / 10482

页数：13

相关论文

共 42 条

[1] NEW HETEROARENES - SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF INDOLIZINO[6,5,4,3-AIJ]QUINOLINE (ULLAZINE) AND OF SOME DERIVATIVES [J].

BALLI, H ;

ZELLER, M .

HELVETICA CHIMICA ACTA, 1983, 66 (07) :2135-2139

[2] Simultaneous fluorescence and redox modulation in an irreversible photochrome based on a strained dibenzo-acridinium cation [J].

Benniston, Andrew C. ;

Rewinska, Dorota B. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (21) :3886-3888

[3] Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics [J].

Berger, Reinhard ;

Wagner, Manfred ;

Feng, Xinliang ;

Muellen, Klaus .

CHEMICAL SCIENCE, 2015, 6 (01) :436-441

[4] Synthesis and Properties of Aza-ullazines [J].

Boldt, Sebastian ;

Parpart, Silvio ;

Villinger, Alexander ;

Ehlers, Peter ;

Langer, Peter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (16) :4575-4578

[5] Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report) [J].

Brouwer, Albert M. .

PURE AND APPLIED CHEMISTRY, 2011, 83 (12) :2213-2228

[6] The Larger Linear N-Heteroacenes [J].

Bunz, Uwe H. F. .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (06) :1676-1686

[7] The larger N-heteroacenes [J].

Bunz, Uwe H. F. .

PURE AND APPLIED CHEMISTRY, 2010, 82 (04) :953-968

[8] Ullazine-based materials: towards novel opportunities in organic electronics [J].

Cebrian, Cristina .

JOURNAL OF MATERIALS CHEMISTRY C, 2018, 6 (44) :11943-11950

[9] Synthesis of pyrrolo[1,2-a]quinolines and ullazines by visible light mediated one- and twofold annulation of N-arylpyrroles with arylalkynes [J].

Das, Amrita ;

Ghosh, Indrajit ;

Koenig, Burkhard .

CHEMICAL COMMUNICATIONS, 2016, 52 (56) :8695-8698

[10] Experimental and DFT Studies Explain Solvent Control of C-H Activation and Product Selectivity in the Rh(III)-Catalyzed Formation of Neutral and Cationic Heterocycles [J].

Davies, David L. ;

Ellul, Charles E. ;

Macgregor, Stuart A. ;

McMullin, Claire L. ;

Singh, Kuldip .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (30) :9659-9669

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