Ring-Fused 1,4-Dihydro[1,2,4]triazin-4-yls through Photocyclization

被引：23

作者：

Bartos, Paulina ^{[1
]}

Young, Victor G., Jr. ^{[4
]}

Kaszynski, Piotr ^{[1
,2
,3
]}

机构：

[1] Univ Lodz, Fac Chem, PL-91403 Lodz, Poland

[2] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland

[3] Middle Tennessee State Univ, Dept Chem, Murfreesboro, TN 37132 USA

[4] Univ Minnesota, Dept Chem, Xray Crystallog Lab, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 10期

关键词：

GRAPHITE RIBBONS; DERIVATIVES; RADICALS; PLANAR; DIARYLETHENES; PHENACENES; STRATEGIES; MEMORIES; COLUMNAR; FAMILY;

D O I：

10.1021/acs.orglett.0c01074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Halogen lamp irradiation of benzo[e][1,2,4]triazines 2[X] in CH2Cl2 solutions leads to planar ring-fused 1,4-dihydro[1,2,4]triazin-4-yl radicals 1 through a novel, potentially general, cyclization mechanism. The scope and efficiency of the method were established for unsubstituted and ortho-substituted (X = NH2, Br, NO2) phenoxy, naphthyloxy, and quinolinoxy derivatives 2[X]. The regioselectivity of 2[X] photocyclization was rationalized with DFT computational methods. Radicals 1 were characterized by spectroscopic (UV-vis, EPR), electrochemical, and XRD methods.

引用

收藏

页码：3835 / 3840

页数：6

相关论文

共 49 条

[1] Functional Planar Blatter Radical through Pschorr-Type Cyclization [J].

Bartos, Paulina ;

Anand, Bindushree ;

Pietrzak, Anna ;

Kaszynski, Piotr .

ORGANIC LETTERS, 2020, 22 (01) :180-184

[2] Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom [J].

Begunov, R. S. ;

Ryzvanovich, G. A. .

RUSSIAN CHEMICAL REVIEWS, 2013, 82 (01) :77-97

[3] Robust Organic Radical Molecular Junctions Using Acetylene Terminated Groups for C-Au Bond Formation [J].

Bejarano, Francesc ;

Olavarria-Contreras, Ignacio Jose ;

Droghetti, Andrea ;

Rungger, Ivan ;

Rudnev, Alexander ;

Gutierrez, Diego ;

Mas-Torrent, Marta ;

Veciana, Jaume ;

van der Zant, Herre S. J. ;

Rovira, Concepci ;

Burzuri, Enrique ;

Crivillers, Nuria .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (05) :1691-1696

[4] Route to Benzo- and Pyrido-Fused 1,2,4-Triazinyl Radicals via N′-(Het)aryl-N′[2-nitro(het)aryl]hydrazides [J].

Berezin, Andrey A. ;

Zissimou, Georgia ;

Constantinides, Christos P. ;

Beldjoudi, Yassine ;

Rawson, Jeremy M. ;

Koutentis, Panayiotis A. .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) :314-327

[5] Synthesis and properties of imidazolo-fused benzotriazinyl radicals [J].

Berezin, Andrey A. ;

Constantinides, Christos P. ;

Mirallai, Styliana I. ;

Manoli, Maria ;

Cao, Levy L. ;

Rawson, Jeremy M. ;

Koutentis, Panayiotis A. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (39) :6780-6795

[6] From Blatter Radical to 7-Substituted 1,3-Diphenyl-1,4-dihydrothiazolo[5′,4′:4,5]benzo[1,2-e][1,2,4]triazin-4-yls: Toward Multifunctional Materials [J].

Berezin, Andrey A. ;

Constantinides, Christos P. ;

Drouza, Chryssoula ;

Manoli, Maria ;

Koutentis, Panayiotis A. .

ORGANIC LETTERS, 2012, 14 (21) :5586-5589

[7]

BLATTER HM, 1968, TETRAHEDRON LETT, P2701

[8] Functional Group Transformations in Derivatives of 1,4-Dihydrobenzo[1,2,4]triazinyl Radical [J].

Bodzioch, Agnieszka ;

Zheng, Minyan ;

Kaszynski, Piotr ;

Utecht, Greta .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7294-7310

[9] Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications [J].

Cardona, Claudia M. ;

Li, Wei ;

Kaifer, Angel E. ;

Stockdale, David ;

Bazan, Guillermo C. .

ADVANCED MATERIALS, 2011, 23 (20) :2367-2371

[10] A Derivative of the Blatter Radical as a Potential Metal-Free Magnet for Stable Thin Films and Interfaces [J].

Ciccullo, F. ;

Gallagher, N. M. ;

Geladari, O. ;

Chasse, T. ;

Rajca, A. ;

Casu, M. B. .

ACS APPLIED MATERIALS & INTERFACES, 2016, 8 (03) :1805-1812

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