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喹喔啉无过渡金属合成的最新进展。

Recent advances in the transition-metal-free synthesis of quinoxalines.

作者信息

Borah Biplob, Chowhan L Raju

机构信息

School of Applied Material Sciences, Centre for Applied Chemistry, Central University of Gujarat Gandhinagar-382030 India

出版信息

RSC Adv. 2021 Nov 19;11(59):37325-37353. doi: 10.1039/d1ra06942j. eCollection 2021 Nov 17.

Abstract

Quinoxalines, also known as benzo[]pyrazines, constitute an important class of nitrogen-containing heterocyclic compounds as a result of their widespread prevalence in natural products, biologically active synthetic drug candidates, and optoelectronic materials. Owing to their importance and chemists' ever-increasing imagination of new transformations of these products, tremendous efforts have been dedicated to finding more efficient approaches toward the synthesis of quinoxaline rings. The last decades have witnessed a marvellous outburst in modifying organic synthetic methods to create them sustainable for the betterment of our environment. The exploitation of transition-metal-free catalysis in organic synthesis leads to a new frontier to access biologically active heterocycles and provides an alternative method from the perspective of green and sustainable chemistry. Despite notable developments achieved in transition-metal catalyzed synthesis, the high cost involved in the preparation of the catalyst, toxicity, and difficulty in removing it from the final products constitute disadvantageous effects on the atom economy and eco-friendly nature of the transformation. In this review article, we have summarized the recent progress achieved in the synthesis of quinoxalines under transition-metal-free conditions and cover the reports from 2015 to date. This aspect is presented alongside the mechanistic rationalization and limitations of the reaction methodologies. The scopes of future developments are also highlighted.

摘要

喹喔啉,也被称为苯并吡嗪,由于其在天然产物、具有生物活性的合成药物候选物以及光电子材料中广泛存在,因而构成了一类重要的含氮杂环化合物。鉴于它们的重要性以及化学家们对这些产物新转化方式不断增长的想象力,人们付出了巨大努力来寻找更有效的喹喔啉环合成方法。在过去几十年里,为了使有机合成方法更具可持续性以改善我们的环境,人们在改进有机合成方法方面取得了惊人的进展。在有机合成中开发无过渡金属催化为获取具有生物活性的杂环开辟了一个新领域,并从绿色和可持续化学的角度提供了一种替代方法。尽管在过渡金属催化合成方面取得了显著进展,但催化剂制备过程中涉及的高成本、毒性以及从最终产物中去除催化剂的困难,对转化反应的原子经济性和环境友好性产生了不利影响。在这篇综述文章中,我们总结了在无过渡金属条件下喹喔啉合成方面取得的最新进展,并涵盖了2015年至今的相关报道。这一方面还伴随着反应方法的机理合理化和局限性。同时也突出了未来发展的方向。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8409/9043781/8bf443b10ea6/d1ra06942j-f1.jpg

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