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<p>The cyclocondensation of 2-aminobenzamide with 3,4-dimethoxypyridine-2-carbaldehyde affords a mixture of 2-(3,4-dimethoxypyridin-2-yl)-2,3-dihydroquinazolin-4(1<i>H</i>)-one and its open-chain tautomer. The dehydrogenation of these compounds with benzoquinones (DDQ, chloranil) as oxidants, giving 2-(pyridin-2-yl)quinazolin-4(3<i>H</i>)-ones, is accompanied by the demethylation of the methoxy group at the C(3) position of the 2-pyridyl moiety. When using 2-methoxy- or 2,3,4-trimethoxybenzaldehydes as deaza analogs of this aldehyde, the demethylation does not occur in the last step regardless of the nature of the oxidant.</p>

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3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step

  • 期刊论文

  • 发表日期：

    2025年2月1日

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  • E. S. Starnovskaya,
  • A. L. Muzyka,
  • A. A. Yurtaeva,
  • A. E. Kopotilova,
  • D. S. Kopchuk,
  • V. S. Gaviko,
  • O. S. Taniya,
  • E. V. Nosova,
  • G. V. Zyryanov,
  • V. L. Rusinov

摘要

The cyclocondensation of 2-aminobenzamide with 3,4-dimethoxypyridine-2-carbaldehyde affords a mixture of 2-(3,4-dimethoxypyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one and its open-chain tautomer. The dehydrogenation of these compounds with benzoquinones (DDQ, chloranil) as oxidants, giving 2-(pyridin-2-yl)quinazolin-4(3H)-ones, is accompanied by the demethylation of the methoxy group at the C(3) position of the 2-pyridyl moiety. When using 2-methoxy- or 2,3,4-trimethoxybenzaldehydes as deaza analogs of this aldehyde, the demethylation does not occur in the last step regardless of the nature of the oxidant.