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

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

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

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.

Original language	English (US)
Article number	SS-2012-M0793-OP
Pages (from-to)	459-462
Number of pages	4
Journal	Synthesis (Germany)
Volume	45
Issue number	4
DOIs	https://doi.org/10.1055/s-0032-1317983
State	Published - 2013

Keywords

cyclization
multicomponent reaction
oxidation
selenium
tandem reaction

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0032-1317983

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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.",

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AU - Denning, Christine R.

AU - Hulme, Christopher

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - cyclization

KW - multicomponent reaction

KW - oxidation

KW - selenium

KW - tandem reaction

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JF - Synthesis (Germany)

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ER -

One-pot two-step synthesis of quinoxalinones and diazepinones via a tandem oxidative amidation-deprotection-cyclization sequence

Abstract

Keywords

ASJC Scopus subject areas

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