Byproduct-Free, One-Pot Synthesis of Ortho Hydroxy Aryl Assimilated Dihydropyrimidones Over-Engineered Sulfonated Graphene Oxide at Room Temperature

IF 3.7 2区 化学 Q2 CHEMISTRY, APPLIED
Sushil R. Mathapati, Mantosh B. Swami, Vijaykumar S. More, Ashutosh Pandey, Suman Kusuma, Arvind H. Jadhav
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Abstract

Dihydropyrimidinones (DHPMs) are an important class of heterocyclic compounds that exhibit a wide range of biological activities. They serve as a key structural motif in pharmaceuticals and agrochemicals, making their efficient and sustainable synthesis highly desirable. The nucleophilic nature of hydroxy groups often alters the reaction pathway towards the formation of oxygen-bonded tetracyclic derivatives and lactonization by-products, which is a significant challenge for the synthesis of dihydropyrimidinone derivatives (DHPM) with ortho-hydroxy groups. In the present study, a highly promising and environmentally friendly protocol has been developed for the synthesis of DHPM derivatives using sulfonated graphene oxide (GO-HSO3) as a metal-free heterogeneous catalyst. The reaction proceeded in ethanol at room temperature, rendering a sustainable and greener approach. The catalytic system efficiently facilitated the Biginelli reactions between ethyl acetoacetate, urea, and azo salicylaldehyde or salicylaldehyde, leading to the selective transformation of DHPMs with excellent yields (84–94%) and minimal byproducts. The superior catalytic activity of GO-HSO3 is attributed to its abundant –SO3H functional groups, which enhance the proton donation and reaction kinetics. This approach is a sustainable and practical method for DHPM synthesis due to its excellent yield, ease of execution, reusability of the catalyst, and adherence to green chemistry principles. Compared to conventional methods that yield an undesired side product, this approach ensures high selectivity and cleaner synthesis. The developed strategy not only aligns with the principle but also demonstrates the potential of sulfonated graphene oxides as a sustainable catalyst for organic transformations.

Abstract Image

室温下无副产物,一锅合成邻羟基芳基同化二氢嘧啶过度工程磺化氧化石墨烯
二氢嘧啶(dhpm)是一类重要的杂环化合物,具有广泛的生物活性。它们是制药和农用化学品的关键结构基序,使其高效和可持续的合成非常可取。羟基的亲核性质经常改变反应途径,形成氧键四环衍生物和内酯化副产物,这是合成邻羟基二氢嘧啶酮衍生物(DHPM)的一个重大挑战。在目前的研究中,利用磺化氧化石墨烯(GO-HSO3)作为无金属异相催化剂,开发了一种非常有前途的环保方案来合成DHPM衍生物。该反应在室温下在乙醇中进行,呈现出一种可持续和更环保的方法。该催化体系有效地促进了乙酰乙酸乙酯、尿素和偶氮水杨醛或水杨醛之间的Biginelli反应,导致dhpm的选择性转化,收率高(84-94%),副产物少。GO-HSO3具有优异的催化活性是由于其丰富的-SO3H官能团增强了质子给能和反应动力学。由于该方法收率高,易于操作,催化剂可重复使用,并且符合绿色化学原则,因此是一种可持续和实用的合成DHPM的方法。与产生不希望的副产物的传统方法相比,这种方法确保了高选择性和更清洁的合成。开发的策略不仅符合原理,而且还展示了磺化氧化石墨烯作为有机转化可持续催化剂的潜力。
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来源期刊
Applied Organometallic Chemistry
Applied Organometallic Chemistry 化学-无机化学与核化学
CiteScore
7.80
自引率
10.30%
发文量
408
审稿时长
2.2 months
期刊介绍: All new compounds should be satisfactorily identified and proof of their structure given according to generally accepted standards. Structural reports, such as papers exclusively dealing with synthesis and characterization, analytical techniques, or X-ray diffraction studies of metal-organic or organometallic compounds will not be considered. The editors reserve the right to refuse without peer review any manuscript that does not comply with the aims and scope of the journal. Applied Organometallic Chemistry publishes Full Papers, Reviews, Mini Reviews and Communications of scientific research in all areas of organometallic and metal-organic chemistry involving main group metals, transition metals, lanthanides and actinides. All contributions should contain an explicit application of novel compounds, for instance in materials science, nano science, catalysis, chemical vapour deposition, metal-mediated organic synthesis, polymers, bio-organometallics, metallo-therapy, metallo-diagnostics and medicine. Reviews of books covering aspects of the fields of focus are also published.
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