Departamento de Química Orgánica I, Facultad de Farmacia and Centro de Investigación Lascaray (Lascaray Research Center), Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), Paseo de la Universidad 7, 01006, Vitoria-Gasteiz, Spain.
Top Curr Chem (Cham). 2023 May 30;381(4):20. doi: 10.1007/s41061-023-00428-7.
Nitrogen heterocycles are part of the structure of natural products and agents with important biological activity, such as antiviral, antibiotic, and antitumor drugs. For this reason, heterocyclic compounds are one of today's most desirable synthetic targets and the Povarov reaction is a powerful synthetic tool for the construction of highly functionalized heterocyclic systems. This process involves an aromatic amine, a carbonyl compound, and an olefin or acetylene to give rise to the formation of a nitrogen-containing heterocycle. This review illustrates advances in the synthetic aspects of the intramolecular Povarov reaction for the construction of intricate nitrogen-containing polyheterocyclic compounds. This original review presents research done in this field, with references to important works by internationally relevant research groups on this current topic, covering the literature from 1992 to 2022. The intramolecular Povarov reactions are described here according to the key processes involved, using different combinations of aromatic or heteroaromatic amines, and aliphatic, aromatic, or heteroaromatic aldehydes. Some catalytic reactions promoted by transition metals are detailed, as well as the oxidative Povarov reaction and some asymmetric intramolecular Povarov processes.
氮杂环是天然产物和具有重要生物活性的药物(如抗病毒、抗生素和抗肿瘤药物)结构的一部分。出于这个原因,杂环化合物是当今最受欢迎的合成目标之一,而 Povarov 反应是构建高度功能化杂环系统的强大合成工具。该过程涉及芳族胺、羰基化合物和烯烃或炔烃,从而形成含氮杂环。本文综述了用于构建复杂含氮多杂环化合物的分子内 Povarov 反应的合成方面的进展。这篇原创综述介绍了该领域的研究成果,参考文献为国际相关研究小组在这一当前课题上的重要著作,涵盖了 1992 年至 2022 年的文献。根据所涉及的关键过程,本文按照使用不同组合的芳族或杂芳族胺以及脂肪族、芳族或杂芳族醛的分子内 Povarov 反应进行了描述。详细介绍了一些过渡金属促进的催化反应,以及氧化 Povarov 反应和一些不对称分子内 Povarov 反应。