Sushil R. Mathapati, Mantosh B. Swami, Vijaykumar S. More, Ashutosh Pandey, Suman Kusuma, Arvind H. Jadhav
{"title":"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","authors":"Sushil R. Mathapati, Mantosh B. Swami, Vijaykumar S. More, Ashutosh Pandey, Suman Kusuma, Arvind H. Jadhav","doi":"10.1002/aoc.70372","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>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-HSO<sub>3</sub>) 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-HSO<sub>3</sub> is attributed to its abundant –SO<sub>3</sub>H 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.</p>\n </div>","PeriodicalId":8344,"journal":{"name":"Applied Organometallic Chemistry","volume":"39 9","pages":""},"PeriodicalIF":3.7000,"publicationDate":"2025-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Byproduct-Free, One-Pot Synthesis of Ortho Hydroxy Aryl Assimilated Dihydropyrimidones Over-Engineered Sulfonated Graphene Oxide at Room Temperature\",\"authors\":\"Sushil R. Mathapati, Mantosh B. Swami, Vijaykumar S. More, Ashutosh Pandey, Suman Kusuma, Arvind H. Jadhav\",\"doi\":\"10.1002/aoc.70372\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>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-HSO<sub>3</sub>) 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-HSO<sub>3</sub> is attributed to its abundant –SO<sub>3</sub>H 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. 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Byproduct-Free, One-Pot Synthesis of Ortho Hydroxy Aryl Assimilated Dihydropyrimidones Over-Engineered Sulfonated Graphene Oxide at Room Temperature
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.
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.