Manganese(III) acetate mediated oxidative radical cyclizations of α-substituted N-[(E)-stilben-2-yl]acetamides

Ghien An Lin; Che Ping Chuang

doi:10.1016/j.tet.2015.05.043

Manganese(III) acetate mediated oxidative radical cyclizations of α-substituted N-[(E)-stilben-2-yl]acetamides

Ghien An Lin, Che Ping Chuang

Department of Chemistry

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

10 Citations (Scopus)

Abstract

A synthetic method of 3-substituted 2-quinolinones from readily available α-substituted N-[(E)-stilben-2-yl]acetamides have been developed. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of N-[(E)-stilben-2-yl]acetamides, undergoes an intramolecular 6-exo-dig cyclization onto the CC bond efficiently and 2-quinolinones was produced. A variety of functional groups, including benzoyl, acetyl, cyano, and ethoxycarbonyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O₂ conditions, these N-[(E)-stilben-2-yl]acetamides were also converted into the corresponding 2-quinolinones effectively and a catalytic amount of manganese(II) acetate was used.

Original language	English
Pages (from-to)	4795-4800
Number of pages	6
Journal	Tetrahedron
Volume	71
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2015.05.043
Publication status	Published - 2015 Jan 1

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "A synthetic method of 3-substituted 2-quinolinones from readily available α-substituted N-[(E)-stilben-2-yl]acetamides have been developed. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of N-[(E)-stilben-2-yl]acetamides, undergoes an intramolecular 6-exo-dig cyclization onto the CC bond efficiently and 2-quinolinones was produced. A variety of functional groups, including benzoyl, acetyl, cyano, and ethoxycarbonyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O2 conditions, these N-[(E)-stilben-2-yl]acetamides were also converted into the corresponding 2-quinolinones effectively and a catalytic amount of manganese(II) acetate was used.",

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N2 - A synthetic method of 3-substituted 2-quinolinones from readily available α-substituted N-[(E)-stilben-2-yl]acetamides have been developed. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of N-[(E)-stilben-2-yl]acetamides, undergoes an intramolecular 6-exo-dig cyclization onto the CC bond efficiently and 2-quinolinones was produced. A variety of functional groups, including benzoyl, acetyl, cyano, and ethoxycarbonyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O2 conditions, these N-[(E)-stilben-2-yl]acetamides were also converted into the corresponding 2-quinolinones effectively and a catalytic amount of manganese(II) acetate was used.

AB - A synthetic method of 3-substituted 2-quinolinones from readily available α-substituted N-[(E)-stilben-2-yl]acetamides have been developed. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of N-[(E)-stilben-2-yl]acetamides, undergoes an intramolecular 6-exo-dig cyclization onto the CC bond efficiently and 2-quinolinones was produced. A variety of functional groups, including benzoyl, acetyl, cyano, and ethoxycarbonyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O2 conditions, these N-[(E)-stilben-2-yl]acetamides were also converted into the corresponding 2-quinolinones effectively and a catalytic amount of manganese(II) acetate was used.

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