Ring opening and skeletal reconstruction of 3-vinyl benzofuranone-chromone synthons: catalyst-free access to skeletally-diverse 2-pyridone and optically active imidazoline derivatives

An efficient regioselective synthesis of tetrasubstituted 3imidazolines under organo-photocatalytic conditions has been developed through formal [3 + 2]-cycloaddition between 2Hazirines and N-tosyl benzylidene imines. The products were isolated in high yields and as a separable mixture of diaster-eoisomers in most of the cases. The mild reaction conditions employing an organic dye as photocatalyst, excellent functional group tolerance, and high regioselectivity are notable features of the current protocol.

show abstract

Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Mishra

Shruti

Kant

et al. 2022

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Liu,

He,

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

A concise and practicable route to the synthesis of multisubstituted 2‐pyridones via a four‐component one‐pot stepwise cyclization catalyzed by Cs2CO3 has been developed. During this stepwise transformation, two new C‐C bonds and two new C‐N bonds were generated through an intermolecular condensation/aza‐Michael reaction/intermolecular Michael addition/intramolecular cyclization sequence. The alternative protocol offers a complementary route to provide a series of structurally diverse polysubstituted 2‐pyridones (21 examples) in good to excellent yields (52–81%) from easily available raw materials arylamines, dialkyl acetylenedicarboxylate, 1,3‐dicarbonyl compounds, and trialkyl orthoformate under mild conditions. It might provide new opportunities for the discovery of 2‐pyridones‐containing drugs.

show abstract

Lewis Acid-Catalyzed Benzannulation of Vinyloxiranes with 3-Formylchromones or 1,4-Quinones for Diversely Functionalized 2-Hydroxybenzophenones, 1,4-Naphthoquinones, and Anthraquinones

Gim,

Rubio,

Mohandoss

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A facile and convenient protocol for the regioselective construction of functionalized 2-hydroxybenzophenones is described. This protocol involves the Sc(OTf) 3 /BF 3 •OEt 2 -catalyzed benzannulation of 2-vinyloxirans with 3-formylchromone, which involves cascade in situ diene formation, [4 + 2] cycloaddition, elimination, and ringopening strategies. Moreover, it provides an expedited synthetic pathway to access biologically intriguing 1,4-naphthoquinones and anthraquinones including vitamin K3 and tectoquinone. The synthesized compounds also hold potential for use as UV filters and show promise as chemosensors for Cu 2+ and Mg 2+ ions.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Ring opening and skeletal reconstruction of 3-vinyl benzofuranone-chromone synthons: catalyst-free access to skeletally-diverse 2-pyridone and optically active imidazoline derivatives

Abstract: Herein is reported the first example of ring opening and skeletal reconstruction of 3-vinyl benzofuranone-chromones 1 as versatile synthons for the synthesis of functionalized 2-pyridones 3 in good to excellent yields.

Cited by 4 publications

References 80 publications

Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Lewis Acid-Catalyzed Benzannulation of Vinyloxiranes with 3-Formylchromones or 1,4-Quinones for Diversely Functionalized 2-Hydroxybenzophenones, 1,4-Naphthoquinones, and Anthraquinones

Contact Info

Product

Resources

About

Ring opening and skeletal reconstruction of 3-vinyl benzofuranone-chromone synthons: catalyst-free access to skeletally-diverse 2-pyridone and optically active imidazoline derivatives

Abstract: Herein is reported the first example of ring opening and skeletal reconstruction of 3-vinyl benzofuranone-chromones 1 as versatile synthons for the synthesis of functionalized 2-pyridones 3 in good to excellent yields.

Cited by 4 publications

References 80 publications

Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Visible Light Organo‐Photocatalytic Synthesis of 3‐Imidazolines

Cs2CO3‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones

Lewis Acid-Catalyzed Benzannulation of Vinyloxiranes with 3-Formylchromones or 1,4-Quinones for Diversely Functionalized 2-Hydroxybenzophenones, 1,4-Naphthoquinones, and Anthraquinones

Contact Info

Product

Resources

About

Cs₂CO₃‐Catalyzed Multi‐Component One‐Pot Stepwise Route for the Synthesis of Polysubstituted 2‐Pyridones