FeCl3-catalyzed regioselective ring-opening of aryl oxirane with 4-hydroxycoumarin for the synthesis of furo[3,2-c]coumarins‡
Literature Information
Publication Date
2023-11-22
DOI
10.1039/D3OB01721D
Impact Factor
3.876
Authors
Simra Faraz, Ahmad Ali, Abu Taleb Khan
View Original
Abstract
The regioselective ring-opening of aryl oxiranes was investigated with various 4-hydroxycoumarins in dimethyl sulfoxide in the presence of 20 mol% FeCl3 as a catalyst at 110 °C. This approach provided a short and concise synthetic route for the regioselective synthesis of 2-aryl-4H-furo[3,2-c] coumarin derivatives. Product formation occurred through regioselective ring-opening of the aryl oxirane at a less hindered site, followed by dehydration and concomitant cyclization. The salient features of our protocol were: cost-effectiveness; short reaction time; step- and atom economy; easy handling; broad scope of substrates; regioselectivity; good-to-excellent yields; non-requirement of dry solvents, co-catalysts, ligands, or any other additives; inert atmospheric conditions.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
![4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure](https://static.chemtradehub.com/structs/104/1041852-85-0-fb1c.webp "4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide structure")
4-[(2-Fluoro-4-methylphenyl)amino]-6-[4-(2-hydroxyethyl)-1-piperazinyl]-7-methoxy-3-cinnolinecarboxamide
CAS Number:
1041852-85-0
Molecular Formula:
C23H27FN6O3
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