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 4hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2c]coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in si...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 88; no. 7; pp. 4730 - 4742
Main Authors: Sorabad, Ganesh Shivayogappa, Yang, Ding-Yah
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 07.04.2023
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
CONDENSATION
DERIVATIVES
QUINONE METHIDES
ISSN:0022-3263, 1520-6904
Online Access:Get more information
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Summary:A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2c]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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00213