Copper-Catalyzed Tandem Radical Cyclization of 8‑Ethynyl-1-naphthyl-amines for the Synthesis of 2H‑Benzo[e][1,2]thiazine 1,1-Dioxides and its Fluorescence Properties

A copper-catalyzed radical cascade dehydrogenative cyclization of N-tosyl-8-ethynyl-1-naphthylamines under air is described herein for the synthesis of thioazafluoranthenes. The reaction proceeds smoothly with high efficiency and a broad reaction scope. The product is indeed a new fluorophore and it...

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Published inJournal of organic chemistry Vol. 85; no. 19; pp. 12526 - 12534
Main Authors Chen, Xia, Zhang, Lianpeng, Wang, Yuzhe, Qiu, Guanyinsheng, Liang, Qinghui, Zhou, Hongwei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INHIBITORS
FLUORANTHENES
ALKYNE
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Summary:A copper-catalyzed radical cascade dehydrogenative cyclization of N-tosyl-8-ethynyl-1-naphthylamines under air is described herein for the synthesis of thioazafluoranthenes. The reaction proceeds smoothly with high efficiency and a broad reaction scope. The product is indeed a new fluorophore and its photophysical properties are also investigated. Based on the results, we are pleased to find that the Stokes shift of amino-linked thioazafluoranthenes in dilute tetrahydrofuran is determined to be 143 nm (4830 cm–1).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01725