Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes

Noguchi, Teppei; Nishii, Yuji; Miura, Masahiro

Synthesis (Germany), 2019, 51(1), 258-270

Number of Access:567（2025-08-15 09:42 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92690

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Title
Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes
Creator
CreatorName
Noguchi, Teppei
NRID
1000070773787 1000070773787
ORCID
0000-0002-6824-0639 0000-0002-6824-0639
researchmap permalink
y_nishii y_nishii
Scopus Author ID
55233363700 55233363700
CreatorName
Nishii, Yuji
NRID
1000020183626 1000020183626
ORCID
0000-0001-8288-6439 0000-0001-8288-6439
researchmap permalink
read0013936 read0013936
Scopus Author ID
7402799909 7402799909
CreatorName
Miura, Masahiro
Subject
annulative coupling
C-H activation
isoquinoline
polyaromatic compounds
rhodium catalyst
Description
Noguchi T., Nishii Y., Miura M.. Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes. Synthesis (Germany) 51, 258 (2019); https://doi.org/10.1055/s-0037-1610376.
Abstract
A rhodium-catalyzed cascade annulative coupling of 3,5-diarylisoxazoles with three equivalents of an alkyne proceeds smoothly in the presence of a Cu(II) oxidant, where the sequential construction of isoquinoline and naphtho[1,8- bc ]pyran frameworks connected by a biaryl linkage is achieved by a single operation. Most of the obtained polycyclic compounds exhibit visible fluorescence in both the solution and the solid state. The hexaphenylated isoquinoline-naphthopyran conjugate (R = Ph) as a representative product shows a green emission which can be turned off by making an isoquinolinium salt with an acid. The emission is also reversibly turned on by treatment with a base.
Publisher
Georg Thieme Verlagiaorl@iaorl.org
Source Title
Synthesis (Germany)
Volume (Issue)
51(1)
Page
258-270
Date of Issued
2019-01-01
Language
English
Handle URL
https://hdl.handle.net/11094/92690
PISSN
00397881
eISSN
1437210X
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1055/s-0037-1610376
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article