A versatile and robust mechanochemical route to Aldehyde–Schiff base conversions has been established for a broad range of aldehydes via a simple cogrinding in mortar with a pestle under a solvent‐free, as well as solvent‐assisted, environment. The extent of amines reactivity under these conditions has also been explored, along with an examination of the possible connection between reactivity and electronic substituent effects. Results obtained demonstrated that the solvent‐free mechanochemical conversion of p‐toluidine and aromatic aldehydes to the corresponding Schiff bases proceeded more smoothly than the corresponding synthesis with 4‐aminobenzonitrile. The present approach not only provides good to excellent yields but also eliminates the disadvantages of the traditional synthesis of Schiff bases, such as the use of hazardous solvents, more or less demand of expensive catalysts, and looking for optimization on reaction conditions.

中文翻译：

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机械化学合成的系统研究：固体芳香伯胺和醛类的席夫碱

通过在无溶剂和溶剂辅助的环境下，用研钵在研钵中进行简单的共研磨，已建立了广泛的，鲁棒的机械化学路线，以实现醛-席夫碱的转化。还研究了在这些条件下胺反应性的程度，并研究了反应性与电子取代基效应之间的可能联系。获得的结果表明p的无溶剂机械化学转化甲苯胺和芳族醛到相应的席夫碱的反应要比用4-氨基苄腈进行相应的合成更顺利。本方法不仅提供良好的优良产率，而且消除了传统的席夫碱合成方法的缺点，例如使用危险溶剂，或多或少地需要昂贵的催化剂，以及寻求对反应条件的优化。