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2-芳基咪唑并[1,2 -]嘧啶-5(8)-酮的微波辅助合成及功能化

Microwave-assisted synthesis and functionalization of 2-arylimidazo[1,2-]pyrimidin-5(8)-ones.

作者信息

Camargo Delascar, Cifuentes Carlos, Castillo Juan-Carlos, Portilla Jaime

机构信息

Bioorganic Compounds Research Group, Department of Chemistry, Universidad de Los Andes Carrera 1 No. 18A-10 Bogotá 111711 Colombia

Escuela de Ciencias Químicas, Universidad Pedagógica y Tecnológica de Colombia Avenida Central del Norte 39-115 Tunja Colombia.

出版信息

RSC Adv. 2024 Jul 15;14(31):22368-22373. doi: 10.1039/d4ra03948c. eCollection 2024 Jul 12.

Abstract

Despite the limited applications and scarcity of commercial examples of imidazo[1,2-]pyrimidines, their exceptional properties hold great potential, representing a significant challenge in discovering more critical applications. Herein, we present a microwave-assisted approach for preparing 2-arylimidazo[1,2-]pyrimidin-5(8)-ones and their alkylation and bromination products using easily accessible and inexpensive reagents, thus offering a promising avenue for further search. Notably, the photophysical properties of an -alkyl derivative were investigated, and the results highlight the high potential of these compounds as modular fluorophores. All the products were obtained with high yields using highly efficient protocols, and the regioselectivity of the reactions was determined on the basis of NMR measurements and X-ray diffraction analysis.

摘要

尽管咪唑并[1,2 - ]嘧啶的应用有限且商业实例稀少,但其卓越性能具有巨大潜力,这在发现更多关键应用方面构成了重大挑战。在此,我们展示了一种微波辅助方法,使用易于获取且价格低廉的试剂制备2 - 芳基咪唑并[1,2 - ]嘧啶 - 5(8) - 酮及其烷基化和溴化产物,从而为进一步探索提供了一条有前景的途径。值得注意的是,对一种 - 烷基衍生物的光物理性质进行了研究,结果突出了这些化合物作为模块化荧光团的高潜力。所有产物均通过高效方案以高产率获得,并且反应的区域选择性是基于核磁共振测量和X射线衍射分析确定的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f338/11247617/d9aa771ad6e4/d4ra03948c-f1.jpg

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