Synthesis of bis-(4-hydroxycoumarin-3-yl)methane using l-glutamic acid.
Journal name: World Journal of Pharmaceutical Research
Original article title: Simple and efficient synthesis of bis-(4- hydroxycoumarin-3-yl)methane derivatives using lglutamic acid as catalyst
The WJPR includes peer-reviewed publications such as scientific research papers, reports, review articles, company news, thesis reports and case studies in areas of Biology, Pharmaceutical industries and Chemical technology while incorporating ancient fields of knowledge such combining Ayurveda with scientific data.
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Bhaskar P. Ankush and Nana V. Shitole
World Journal of Pharmaceutical Research:
(An ISO 9001:2015 Certified International Journal)
Full text available for: Simple and efficient synthesis of bis-(4- hydroxycoumarin-3-yl)methane derivatives using lglutamic acid as catalyst
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
Doi: 10.20959/wjpr20238-28162
Copyright (license): WJPR: All rights reserved
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Summary of article contents:
Introduction
The study explores the synthesis of bis-(4-hydroxycoumarin-3-yl)methane derivatives through a one-pot multicomponent reaction involving various substituted aromatic and heterocyclic aldehydes combined with 4-hydroxycoumarine. The process employs L-Glutamic acid as a catalyst, achieving this in a water-ethanol solvent mixture. The resulting approach is highlighted for its simplicity, efficiency, and environmentally friendly characteristics, producing high yields and minimal toxic waste, thereby offering significant advancements in organic synthesis methods.
L-Glutamic Acid as an Efficient Catalyst
L-Glutamic acid, known as an amino acid, serves as a highly effective catalyst in organic chemistry. Its application in synthesizing various biologically significant compounds has been well-documented. The study presents L-Glutamic acid as a viable alternative to more traditional catalysts, which often pose challenges such as high costs, environmental hazards, and complex operational procedures. The catalytic efficiency was demonstrated through the optimization of various parameters, confirming that even a low concentration (5 mol%) of L-Glutamic acid notably enhances the yields of the desired product, bis-(4-hydroxycoumarin-3-yl)methane.
Simplified Synthetic Procedure
The synthetic procedure for obtaining bis-(4-hydroxycoumarin-3-yl)methane derivatives is straightforward and efficient. By combining 1 mmol of substituted aromatic aldehyde and 2 mmol of 4-hydroxycoumarine, along with a 5 mol% amount of L-Glutamic acid as a catalyst in a 50 ml round-bottom flask, the reaction is conducted under reflux in a 1:1 ethanol-water mixture for a duration of 5 to 40 minutes. The progress of the reaction is easily monitored using thin-layer chromatography (TLC), and upon completion, the product can be isolated and characterized. This method not only results in shorter reaction times but also facilitates simpler workup procedures, highlighting its practical advantages.
Yield and Productivity
The research indicates remarkable yields ranging from 52% to 99%, showcasing the method's effectiveness across a range of substrates. Various derivatives were synthesized successfully, with reaction times and yields systematically recorded, emphasizing the applicability of the method to diverse aromatic substituents. The synthesized compounds were thoroughly characterized through various spectroscopic techniques—FT-IR, NMR, and LC-MS—which confirmed the success of the reactions. The versatility of the synthetic route supports its adoption in further explorations in medicinal chemistry, where such coumarin derivatives are of significant interest due to their biological properties.
Conclusion
In conclusion, the study presents a novel, efficient method for synthesizing bis-(4-hydroxycoumarin-3-yl)methane derivatives using L-Glutamic acid as a catalyst in an eco-friendly solvent system. This approach not only simplifies the synthetic process but also reinforces the growing trend of utilizing green chemistry principles in organic synthesis. The high yields and rapid reaction times position this method as a valuable contribution to the existing methodologies in the field of pharmaceutical and medicinal chemistry, indicating promising avenues for further study and application.
FAQ section (important questions/answers):
What was the primary focus of this study?
The study focuses on synthesizing bis-(4-hydroxycoumarin-3-yl)methane derivatives using L-Glutamic acid as a catalyst through a one-pot-multicomponent reaction of various aldehydes.
What are the advantages of the proposed synthesis method?
The method offers inexpensive reagents, simple procedures, environmentally friendly conditions, short reaction times (5-40 minutes), and excellent yields (52-99%).
How was the reaction progress monitored during the synthesis?
The reaction's progress was monitored using thin-layer chromatography (TLC) on suitable TLC plates under UV light.
What role does L-Glutamic acid play in this study?
L-Glutamic acid serves as an efficient catalyst in synthesizing bis-(4-hydroxycoumarin-3-yl)methane derivatives from substituted aromatic aldehydes and 4-hydroxycoumarine.
What are some compounds synthesized in this study?
The study synthesized various derivatives like 3c, 3d, and 3e, characterized by techniques like IR, NMR, and mass spectrometry.
How were the synthesized products characterized?
The products were characterized using Fourier transform infrared (FT-IR), NMR spectroscopy, and mass spectrometry, confirming their structures through comparison with literature data.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “Synthesis of bis-(4-hydroxycoumarin-3-yl)methane using l-glutamic acid.”. This list explains important keywords that occur in this article and links it to the glossary for a better understanding of that concept in the context of Ayurveda and other topics.
1) Water:
Water is a solvent used in the synthesis of bis-(4-hydroxycoumarin-3-yl)methane derivatives in combination with ethanol (1:1 ratio). It plays a crucial role in facilitating the reaction process by dissolving the reagents and allowing for the efficient catalysis by L-Glutamic acid, thus contributing to the eco-friendly nature of the method.
2) Methane:
Methane, while typically known as a simple hydrocarbon, in this context refers to bis-(4-hydroxycoumarin-3-yl)methane, a compound synthesized through the described methodology. Its presence in the title highlights the focus on synthesizing complex organic molecules that possess biological significance, especially in medicinal chemistry.
3) Table:
Tables are utilized to present organized data and findings clearly. In this study, tables summarize reaction conditions, yield percentages, and optimizations of catalyst amounts or solvent types. This visual representation aids in quickly understanding the results and comparing the effectiveness of various parameters during the experimental procedure.
4) India:
India is the geographical context of this study, where the synthesis of bis-(4-hydroxycoumarin-3-yl)methane derivatives was conducted. The significance lies in the promotion of local research capabilities in organic synthesis and the development of cost-effective and environmentally benign chemical processes beneficial to the country's pharmaceutical sector.
5) Study (Studying):
The phrase 'the study' refers to the specific research work focused on the synthesis of bis-(4-hydroxycoumarin-3-yl)methane derivatives. It highlights the methodology, catalysts used, and results obtained, establishing the significance of this research in terms of improving synthesis efficiency and environmental safety.
6) Shri (Sr, Sri):
The term 'Shri' is an honorific title used in India, often before names to denote respect. In this research context, it precedes the name of the academic institution, 'Shri Shivaji Mahavidyalaya', indicating the author's affiliation and highlighting the importance of educational institutions in advancing scientific research.
7) Rasika (Rashika):
Rasika refers to 'Kai Rasika Mahavidyalaya', the educational institution associated with one of the authors. This designation underscores the role of such institutions in fostering research and development, education, and collaboration in chemistry, leading to significant contributions in the synthesis of valuable organic compounds.
8) Nana (Na-na):
Nana, as a name, refers to one of the authors, Nana V. Shitole, contributing to this research. The inclusion of author names emphasizes the collaborative effort behind the study and acknowledges individual contributions to the findings and methodologies presented in the article.
9) Generality:
Generality pertains to the applicability of the methodology for synthesizing various bis-(4-hydroxycoumarin-3-yl)methane derivatives. This implies that the developed method is versatile and can accommodate different substituted aldehydes, making it an important criterion in evaluating the effectiveness of synthetic procedures in organic chemistry.
10) Discussion:
Discussion in this research context refers to the section where authors analyze, interpret, and contextualize their experimental findings. It includes comparisons with existing literature, evaluation of results, and considerations of the implications of the synthesized compounds in medicinal chemistry, thus elucidating the significance of their work.
11) Pesticide:
Pesticide, in this context, relates to the biological activity of synthesized bis-(4-hydroxycoumarin-3-yl)methane derivatives. This denotes the importance of these compounds in agricultural applications, emphasizing the potential development of eco-friendly pest control agents benefiting sustainable agriculture whilst minimizing harmful chemical residues.
12) Transformation (Transform, Transforming):
Transform signifies the process of converting or synthesizing one compound into another. In this research, transform reflects the chemical transformation of substituted aldehydes and 4-hydroxycoumarine into bis-(4-hydroxycoumarin-3-yl)methane derivatives, showcasing the efficacy of the L-Glutamic acid catalyst in enhancing synthetic routes.
13) Activity:
Activity refers to the biological activities exhibited by the synthesized coumarin derivatives, such as antimicrobial, anti-inflammatory, and anticoagulant properties. This term highlights the significance of these compounds in pharmaceutical research and development, influencing drug design and therapeutic applications based on their biological effectiveness.
14) Lamp:
Lamp refers to the UV lamp mentioned in the methodology, which is used for monitoring the progress of the reaction through thin-layer chromatography (TLC). The use of a lamp provides visual cues for the detection of products, illustrating the importance of analytical techniques in verifying the success of synthetic processes.
Other Science Concepts:
Discover the significance of concepts within the article: ‘Synthesis of bis-(4-hydroxycoumarin-3-yl)methane using l-glutamic acid.’. Further sources in the context of Science might help you critically compare this page with similair documents:
Environmental pollution, Anti-inflammatory activities, Anticancer activity, Anti-microbial activity, Anticoagulant activity, Melting point, Biological activities, TLC plate, Melting point determination, Spectroscopic analysis, Reaction mixture, Organic Chemistry, Coumarin, Short reaction time.