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Abstract <p>The reaction of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with naphthalen-1-amine in the presence of a catalytic amount of acetic acid afforded 1-(2-methylbenzo[<i>h</i>]quinolin-3-yl)ethanone. This transformation was presumed to proceed as a consecutive process including the formation of β-enamino ketone, elimination of alkanethiol from the latter, Friedel–Crafts intramolecular cyclization with the participation of the new double bond, and oxidative aromatization. 1-(Benzo[<i>h</i>]quinolin-3-yl)ethanone was also obtained by the three-component condensation of pentane-2,4-dione, formaldehyde, and naphthalen-1-amine in the presence of acetic acid. In this case, the precursor of 1-(benzo[<i>h</i>]quinolin-3-yl)ethanone is 4-(naphthalen-1-ylamino)pent-3-en-2-one.</p>

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Synthesis of 1-(2-Methylbenzo[h]quinolin-3-yl)ethanone by the Reaction of Pentane-2,4-diones with Naphthalen-1-amine

  • 期刊论文

  • 发表日期：

    2026年3月1日

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  • L. A. Baeva,
  • R. M. Nugumanov,
  • T. R. Nugumanov

摘要

Abstract

The reaction of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with naphthalen-1-amine in the presence of a catalytic amount of acetic acid afforded 1-(2-methylbenzo[h]quinolin-3-yl)ethanone. This transformation was presumed to proceed as a consecutive process including the formation of β-enamino ketone, elimination of alkanethiol from the latter, Friedel–Crafts intramolecular cyclization with the participation of the new double bond, and oxidative aromatization. 1-(Benzo[h]quinolin-3-yl)ethanone was also obtained by the three-component condensation of pentane-2,4-dione, formaldehyde, and naphthalen-1-amine in the presence of acetic acid. In this case, the precursor of 1-(benzo[h]quinolin-3-yl)ethanone is 4-(naphthalen-1-ylamino)pent-3-en-2-one.