Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols?
RSC Advances Pub Date: 2022-07-21 DOI: 10.1039/D2RA03416F
Abstract
Two acid-catalyzed tandem reactions between 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols are described. Depending mainly on the propargylic alcohol used, these tandem reactions proceed via either a Friedel–Crafts-type allenylation followed by 6-endo-dig cyclization sequence to form pyrano[3,2-c]quinolones or a Friedel–Crafts-type alkylation and 5-exo-dig ring closure sequence to afford furo[3,2-c]quinolones in moderate-to-high yields. The pyrano[3,2-c]quinolones products could be further transformed to tetracyclic 4,9-dihydro-5H-cyclopenta[lmn]phenanthridin-5-one derivatives.
![Graphical abstract: Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols](http://scimg.chem960.com/usr/1/D2RA03416F.jpg)
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Journal Name：RSC Advances
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CAS no.: 89640-58-4
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