Multicomponent Coupling Reaction Using Arynes: Synthesis of Xanthene Derivatives

One-pot synthesis of xanthene derivatives was achieved by a route involving the cascade three-component coupling reaction of arynes with DMF and active methylenes followed by the SN2′ reaction of three-component coupling products with thiols. The reactivity of three-component coupling products towar...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 16; pp. 8464 - 8469
Main Authors Yoshioka, Eito, Nishimura, Masatoshi, Nakazawa, Takashi, Kohtani, Shigeru, Miyabe, Hideto
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2015
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Dimethylformamide - chemistry
Molecular Structure
Oxygen - chemistry
Palladium
Physical Sciences
Science & Technology
Sulfhydryl Compounds - chemistry
Xanthenes - chemical synthesis
Xanthenes - chemistry
CYCLOADDITION
INSERTION
3-COMPONENT REACTION
OXYGEN HETEROCYCLES
TERMINAL ALKYNES
SELECTIVE SYNTHESIS
CARBON-CARBON
PI-BOND
STRAIGHTFORWARD ACCESS
BENZYNE
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Summary:One-pot synthesis of xanthene derivatives was achieved by a route involving the cascade three-component coupling reaction of arynes with DMF and active methylenes followed by the SN2′ reaction of three-component coupling products with thiols. The reactivity of three-component coupling products toward nucleophiles and the further conversion of oxygen heterocycles allowing facile incorporation of structural variety were studied.
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.5b01452