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在铜催化合成Pyrrolo[1,2-

Natália M Moreira^1,2, Ingrid T de Miranda¹, Jhonathan R N Dos Santos¹

¹Centre of Excellence for Research in Sustainable Chemistry, Chemistry Department, Federal University of São Carlos, São Carlos, São Paulo 13565-905, Brazil.

The Journal of organic chemistry

|June 5, 2023

概括

这项研究展示了一种使用铜酸盐催化剂的新方法,用于C(sp3) -H功能化的azaarenes. 反应有效地合成了具有潜在生物活性的新型pyrroloquinazolines和isoquinolines.

科学领域:

有机化学有机化学
药用化学医学化学
异环化学异环化学

背景情况:

在N-异环 (azaarenes) 中直接功能化C(sp3) -H键是一个不断增长的研究领域.
现有的方法往往需要苛刻的反应条件,限制了它们的适用性.
开发更温和,更高效的阿扎伦功能化的方法对于合成化学至关重要.

研究的目的:

开发一种新型的催化方法,用于4-甲基基纳和1-基因诺的C(sp3) -H功能化.
合成新的异环化合物,特别是罗[1,2-c]基纳和罗[2,1-a]异类.
评估合成化合物的生物活性,以对抗Plasmodium falciparum.

主要方法:

作为反应伙伴,利用α替代的β-尼托烯.
采用廉价的酸铜作为催化剂.
优化反应条件,以实现高效的C(sp3) -H功能化.

主要成果:

已经成功合成了21种pyrrolo[1,2-c]quinazolines,1种imidazo[1,2-c]quinazoline和4种pyrrolo[2,1-a]isoquinolines.
对于合成的异环化合物,取得了中等到良好的产量.
确定了pyrrolo[1,2-c]quinazolines对抗Plasmodium falciparum的有前途的生物活性.

结论:

开发的铜催化反应为azaarenes的C(sp3) -H功能化提供了一个有效的途径.
该方法允许合成多样化和复杂的含异环.
合成的pyrrolo[1,2-c]quinazolines显示出作为抗疟疾药物的潜力.

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