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

被引：21

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

页码：3835 / 3840

页数：6

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