Synthesis 2013; 45(4): 459-462
DOI: 10.1055/s-0032-1317983
paper
© Georg Thieme Verlag Stuttgart · New York

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

Arthur Y. Shaw
a   Department 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
a   Department 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*
a   Department 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
b   Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721, USA
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Publikationsverlauf

Received: 25. Oktober 2012

Accepted after revision: 12. Dezember 2012

Publikationsdatum:
10. Januar 2013 (online)


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.

Supporting Information