Lewis Acid-Catalyzed 1,4-Addition and Annulation of 4‑Hydroxy-coumarins with o‑Hydroxyphenyl Propargyl Amines: Entry to Regio-Selective Synthesis of Furano[3,2‑c]coumarins and Pyrano[3,2‑c]coumarins

A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano­[3,2-c]­coumarin and pyrano­[3,2-c]­coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the...

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Published inJournal of organic chemistry Vol. 88; no. 7; pp. 4730 - 4742
Main Authors Sorabad, Ganesh Shivayogappa, Yang, Ding-Yah
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.04.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
CONDENSATION
DERIVATIVES
QUINONE METHIDES
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Summary:A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano­[3,2-c]­coumarin and pyrano­[3,2-c]­coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide and is followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano­[3,2-c]­coumarins and pyrano­[3,2-c]­coumarins, respectively. The prepared o-hydroxyl substituted pyrano­[3,2-c]­coumarins could be readily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00213