Reaction of ethyl 2-(arylidene)acetoacetates, 3-methyl-1H-pyrazol-5(4H)-one, and ammonium acetate: Unexpected formation of bis(pyrazolyl)methanes versus fused pyrazolo-1,4-dihydropyridines

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-04-18 DOI:10.1080/00397911.2025.2475908

Adeleh Moshtaghi Zonouz (Supervision) , Nojaba Forghani (Methodology) , Mostafa Razban (Investigation)

引用次数: 0

Abstract

The reaction of 3-methyl-1H-pyrazol-5(4H)-one, ethyl 2-(arylidene)acetoacetates, and ammonium acetate in refluxing ethanol leads to the formation of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazolyl-5-ol) derivatives with high yields, instead of the expected fused pyrazolo-1,4-dihydropyridines. This suggests the presence of a reactive vinylogous imino derivative as an intermediate.

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2-（芳基）乙酰乙酸乙酯、3-甲基- 1h -吡唑-5(4H)- 1和乙酸铵的反应：双（吡唑基）甲烷与融合吡唑-1,4-二氢吡啶的意外形成

在回流乙醇中，3-甲基- 1h -吡唑-5(4H)- 1、2-乙基（芳基）乙酰乙酸酯与乙酸铵反应生成了产率高的4,4 ' -（芳基亚甲基）双（3-甲基- 1h -吡唑-5-醇）衍生物，而不是预期的融合吡唑-1,4-二氢吡啶。这表明存在一种反应性葡萄状亚胺衍生物作为中间体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.