One-Pot Two-Step Synthesis of Quinoxalinones and Diazepinones via a Tandem Oxidative Amidation–Deprotection–Cyclization Sequence

Arthur Y. Shaw; Christine R. Denning; Christopher Hulme

doi:10.1055/s-0032-1317983

Synthesis, Table of Contents

Synthesis 2013; 45(4): 459-462
DOI: 10.1055/s-0032-1317983

paper

One-Pot Two-Step Synthesis of Quinoxalinones and Diazepinones via a Tandem Oxidative Amidation–Deprotection–Cyclization Sequence

Arthur Y. Shaw

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

,

Christine R. Denning

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

,

Christopher Hulme*

^aDepartment of Pharmacology and Toxicology, College of Pharmacy, BIO5 Oro Valley, The University of Arizona, 1580 E. Hanley Blvd., Oro Valley, AZ 85737, USA Fax: +1(520)6260794 Email: hulme@pharmacy.arizona.edu

^bDepartment of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721, USA

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Abstract

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Abstract

This report discloses novel concise syntheses of quinoxalinones and diazepinones via a tandem oxidative amidation–deprotection–cyclization sequence. A selenium dioxide mediated oxidative amidation of arylglyoxals with secondary amines was carried out under microwave irradiation to give the corresponding α-keto amides, followed by an acid-promoted deprotection and cyclization to afford the desired products in moderate to good yields.

Key words

multicomponent reaction - selenium - oxidation - cyclization - tandem reaction

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References

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