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硫酸普罗黄素(PFH):作为一种光敏剂(PS)生物催化剂用于可见光诱导的吡喃并[2,3]嘧啶支架的合成。

Proflavine (PFH): as a photosensitizer (PS) biocatalyst for the visible-light-induced synthesis of pyrano [2,3] pyrimidine scaffolds.

作者信息

Mohamadpour Farzaneh, Amani Ali Mohammad

机构信息

Department of Medical Nanotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical Sciences, Shiraz, Iran.

出版信息

Front Chem. 2024 Mar 26;12:1304850. doi: 10.3389/fchem.2024.1304850. eCollection 2024.

Abstract

A sustainable methodology for the synthesis of pyrano [2,3-] pyrimidine scaffolds have been developed, employing the Knoevenagel-Michael tandem cyclocondensation reaction of barbituric acid/1,3-dimethylbarbituric acid, malononitrile, and aryl aldehydes. This study elucidates the advancement of a sustainable and environmentally conscious approach to synthesizing this category of chemical compounds. In the present investigation, a novel photosensitizer comprising proflavine (PFH) bio-photocatalyst was employed in an aqueous medium, subjected to air atmosphere at room temperature, and stimulated by a blue-light-emitting diode (LED) to harness renewable energy. The fundamental objective of this initiative is to utilize a photosensitizer (PS) biocatalyst that has been recently developed, can be conveniently acquired, and is priced affordably. The proflavine (PFH) photocatalyst, demonstrates the ability to initiate photoinduced-electron transfer (PET) through exposure to visible light. This property endows the photocatalyst with a practical and efficient method of achieving high effectiveness, energy efficiency, and environmentally friendly outcomes. The current research endeavor has the objective of examining the turnover number (TON) and turnover frequency (TOF) pertaining to pyrano [2,3-] pyrimidine scaffolds. Moreover, it has been validated that cyclization at the gram-scale is a feasible approach that can be employed in various industrial settings.

摘要

已开发出一种可持续的方法来合成吡喃并[2,3 - ]嘧啶骨架,该方法采用巴比妥酸/1,3 - 二甲基巴比妥酸、丙二腈和芳醛的Knoevenagel - Michael串联环缩合反应。本研究阐明了一种可持续且具有环境意识的合成这类化合物的方法的进展。在本研究中,一种新型的包含硫酸原黄素(PFH)生物光催化剂的光敏剂在水介质中使用,在室温下置于空气气氛中,并由蓝光发光二极管(LED)激发以利用可再生能源。该举措的基本目标是利用一种最近开发的、易于获得且价格合理的光敏剂(PS)生物催化剂。硫酸原黄素(PFH)光催化剂通过暴露于可见光表现出引发光致电子转移(PET)的能力。这一特性赋予了光催化剂一种实现高效、能源高效和环境友好结果的实用且有效的方法。当前的研究工作旨在研究与吡喃并[2,3 - ]嘧啶骨架相关的周转数(TON)和周转频率(TOF)。此外,已经验证了克级规模的环化是一种可行的方法,可用于各种工业环境。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c144/11002269/3177c5c52603/fchem-12-1304850-g001.jpg

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