A series of pyrano[3,2-]quinolone derivatives has been synthesized in the presence of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst and water as the solvent. The target compounds were synthesized through the three-component reaction between aldehydes, malononitrile/ethylcyanoacetate, and 4-hydroxy-1-methyl-2(1)-quinolone. The advantages of this protocol are excellent yields of products, short reaction times, cost efficiency, atom economy, and a simple work-up procedure with no need for extra purification techniques. Moreover, the catalyst can be easily recovered and reused for up to three cycles without losing any significant activity.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.2c01403DOI Listing

Publication Analysis

Top Keywords

pyrano[32-]quinolone derivatives
8
green bio-organic
8
bio-organic catalyst
8
tandem protocol
4
protocol synthesis
4
synthesis pyrano[32-]quinolone
4
derivatives taurine
4
taurine green
4
catalyst aqueous
4
aqueous medium
4

Similar Publications

Domino Knoevenagel-cyclization reactions of styrene substrates, containing an -(-formyl)aryl subunit, were carried out with -substituted 2-cyanoacetamides to prepare tetrahydro-4-pyrano[3,4-]quinolone and hexahydrobenzo[]phenanthridine derivatives by competing IMHDA and IMSDA cyclization, respectively. The diastereoselective IMHDA step with α,β-unsaturated amide, thioamide, ester and ketone subunits as a heterodiene produced condensed chiral tetrahydropyran or thiopyran derivatives, which in the case of Meldrum's acid were reacted further with amine nucleophiles in a multistep domino sequence. In order to simplify the benzene-condensed tricyclic core of the targets and get access to hexahydro-1-pyrano[3,4-]pyridine derivatives, a truncated substrate was reacted with cyclic and acyclic active methylene reagents in diastereoselective Knoevenagel-IMHDA reactions to prepare novel condensed heterocyclic scaffolds.

View Article and Find Full Text PDF

Herein, we report the development of a diastereoselective and efficient route to construct sugar-derived pyrano[3,2-c]quinolones utilizing 1-C-formyl glycal and 4-hydroxy quinolone annulation. This methodology will open a route to synthesize nature inspired pyrano[3,2-c]quinolones. This is the first report for the stereoselective synthesis of sugar-derived pyrano[3,2-c]quinolones, where 100% stereoselectivity was observed.

View Article and Find Full Text PDF

A series of pyrano[3,2-]quinolone derivatives has been synthesized in the presence of taurine (2-aminoethanesulfonic acid) as a green bio-organic catalyst and water as the solvent. The target compounds were synthesized through the three-component reaction between aldehydes, malononitrile/ethylcyanoacetate, and 4-hydroxy-1-methyl-2(1)-quinolone. The advantages of this protocol are excellent yields of products, short reaction times, cost efficiency, atom economy, and a simple work-up procedure with no need for extra purification techniques.

View Article and Find Full Text PDF

This study deals with the synthesis of the regioselective and facile domino one-pot four-component reaction of 2-chloroquinoline-3-carbaldehydes, 1, 3-cyclodione compounds (as cyclic active methylene), ethyl acetoacetate (as β-keto ester), and hydrazine hydrate in the presence of DABCO as a homogeneous organocatalyst yielding a novel series of 4H-pyrano[2, 3-b]quinolones. This multicomponent reaction has some advantages; the significant one is C-O bond formation under metal-free conditions. Other benefits include simple procedure, mild and green condition, high yield, easy purification, and excellent regioselectivity.

View Article and Find Full Text PDF

Two acid-catalyzed tandem reactions between 4-hydroxy-1-methylquinolin-2(1)-one and propargylic alcohols are described. Depending mainly on the propargylic alcohol used, these tandem reactions proceed either a Friedel-Crafts-type allenylation followed by 6--dig cyclization sequence to form pyrano[3,2-]quinolones or a Friedel-Crafts-type alkylation and 5--dig ring closure sequence to afford furo[3,2-]quinolones in moderate-to-high yields. The pyrano[3,2-]quinolones products could be further transformed to tetracyclic 4,9-dihydro-5-cyclopenta[]phenanthridin-5-one derivatives.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!