An efficient protocol for the synthesis of 1,2,4- triazolo[1,5-a]pyrimidines
Journal name: World Journal of Pharmaceutical Research
Original article title: An efficient protocol for the synthesis of 1,2,4- triazolo[1,5-a]pyrimidines
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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J. P. Chandrani and K. J. Ganatra
World Journal of Pharmaceutical Research:
(An ISO 9001:2015 Certified International Journal)
Full text available for: An efficient protocol for the synthesis of 1,2,4- triazolo[1,5-a]pyrimidines
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
Doi: 10.20959/wjpr201716-10226
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Summary of article contents:
Introduction
In the research article published in the World Journal of Pharmaceutical Research, authors J. P. Chandrani and K. J. Ganatra present an efficient protocol for synthesizing 1,2,4-triazolo[1,5-a]pyrimidine derivatives utilizing 5-amino, 1,2,4-triazole as a building block. The synthesis employs a one-pot Biginelli reaction method, which, although historically noted for variable yields, has regained attention for producing compounds with significant therapeutic potential. This study details the synthesis process and characterization of various derivatives, highlighting advancements that enhance yield and efficiency in using the Biginelli reaction.
Significance of the Biginelli Reaction
The Biginelli reaction, originally reported in 1893, is a cyclocondensation reaction that combines β-keto esters, aldehydes, and urea in an acidic environment. Despite its potential, traditional implementations often result in moderate yields that range from 20% to 50%. Recent studies have intensified efforts to improve this reaction by investigating various catalysts and reaction conditions. The resurgence of interest in this methodology stems from its ability to produce compounds with diverse therapeutic properties, including antitumor activities and anti-fungal effects, thus underscoring its relevance in medicinal chemistry.
Methodology for Synthesis
The authors describe a straightforward and efficient multi-component synthesis of 1,2,4-triazolo[1,5-a]pyrimidines, achieving excellent yields through the use of 3-amino-1,2,4-triazole, aldehydes, and ethyl 3-oxo hexanoate in the presence of a catalytic amount of dimethylformamide. The synthesis process capitalizes on the simplicity of the Biginelli reaction while adhering to a solvent-free approach. Characterization of the products was performed using various spectroscopic techniques, including FT-IR, 1H NMR, and mass spectrometry, ensuring thorough analysis of the newly formed compounds.
Results and Discussion
The researchers conducted systematic tests to optimize the synthesis conditions, comparing various solvents and reaction setups. Ultimately, the best results were observed under solvent-free conditions, with the use of aldehydes that feature electron-donating groups contributing favorably to the yields of the triazolopyrimidine derivatives. Data presented in the results section included detailed spectral information for multiple synthesized compounds, indicating the successful formation of the target molecules and validating their proposed structures.
Conclusion
In conclusion, the research highlights an effective and efficient method for the synthesis of 1,2,4-triazolo[1,5-a]pyrimidines, leveraging readily available starting materials under optimized conditions. The method not only achieves moderate to good yields but also simplifies the reaction process, making it suitable for further explorations in drug development. Acknowledging the support from local institutions, the authors underscore the importance of leveraging collaborative efforts to enhance research capabilities in the field of organic chemistry and pharmacology. This work contributes significantly to the ongoing exploration of Biginelli-type reactions in pharmaceutical applications.
FAQ section (important questions/answers):
What is the focus of the research conducted by Ganatra et al.?
The research focuses on the efficient synthesis of 1,2,4-triazolo[1,5-a]pyrimidine derivatives using a one-pot Biginelli synthesis method. The resulting compounds were characterized using various spectroscopic techniques.
What starting materials were used for the synthesis of triazolopyrimidines?
The synthesis utilized 3-amino-1,2,4-triazole, aldehydes, and ethyl 3-oxo hexanoate. The process involved a catalytic amount of dimethylformamide to enhance the reaction efficiency.
What spectroscopic techniques were employed for compound characterization?
Characterization of the synthesized compounds was achieved using FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. These techniques provided valuable insights into the molecular structure of the derivatives.
What were the reported yields of the synthesized triazolopyrimidines?
The synthesized triazolopyrimidines exhibited moderate to good yields, ranging from approximately 60% to 88%, depending on the specific compound and its substituents.
What are the potential applications of 1,2,4-triazolo[1,5-a]pyrimidines?
1,2,4-triazolo[1,5-a]pyrimidines have therapeutic and pharmacological properties, including antitumor potency and inhibition of KDR kinase. Their efficacy makes them promising candidates for further medicinal chemistry exploration.
How were the reaction conditions optimized in the synthesis?
Various solvents and conditions were tested, revealing that solvent-free reactions at 100°C yielded the best results. This optimization improved the efficiency of the synthesis process significantly.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “An efficient protocol for the synthesis of 1,2,4- triazolo[1,5-a]pyrimidines”. 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) Science (Scientific):
Science is the systematic study of the structure and behavior of the physical and natural world through observation and experimentation. In this article, it relates to the synthesis of chemical compounds and the methodologies used to explore their properties and potential applications in pharmaceuticals.
2) Table:
In the context of this article, a table is utilized to present data clearly and concisely. Specifically, it organizes information about synthesized compounds, their molecular formulas, molecular weights, and yield percentages, allowing for easy comparisons and an efficient overview of the research findings.
3) Pharmacological:
Pharmacological refers to the study of how drugs interact with biological systems. This article discusses derivatives that exhibit significant pharmacological properties, including antitumor effects and inhibition of specific enzymes, thereby emphasizing the importance of developing new pharmaceutical agents through synthesis.
4) Saurashtra (Saurastra):
Saurashtra is a region in the western Indian state of Gujarat. The mention of Saurashtra University indicates the collaboration of local academic institutions in research efforts. The region contributes to the scientific community by supporting research and development in pharmaceutical science.
5) Discussion:
Discussion in academic writing involves analyzing and interpreting the results of research. Here, it provides insights into how varying conditions, such as the use of solvents and catalysts, impact synthesis processes and yields, driving home the significance of optimizing chemical reaction conditions in pharmaceutical synthesis.
6) Semiramis:
Semiramis is a name that appears in the context of a referenced author in the article. In scientific literature, citing authors contributes to establishing credibility, as their prior research supports the findings presented. This highlights the collaborative nature of scientific research across various studies.
7) Kalita:
Kalita refers to an author mentioned in the references. Citing authors enhances the research's reliability by connecting it to established work in the field. This connection shows that the synthesis of triazolopyrimidines builds on prior pharmacological studies, thereby contextualizing the relevance of the current research.
8) Maurya:
Maurya is another cited author, signifying contributions to the body of knowledge regarding the synthesis and functions of chemical compounds. By referencing prior literature, the article underscores a collaborative narrative within the scientific community, emphasizing shared goals in advancing pharmaceutical research.
9) Dodiya:
Dodiya, like other authors mentioned, is referenced to establish a scholarly context in which the current study operates. This aids in building a link between different research endeavors, pointing toward collaborative efforts in understanding the chemistry of triazolopyrimidine derivatives and their applications.
10) Indian:
The term Indian in this context identifies the geographical and cultural context of the research. It may indicate that the authors are based in India and that their work contributes to local and national scientific advancement, reflecting the global pursuit of knowledge in pharmaceutical sciences.
11) Kumar:
Kumar is mentioned as an author whose previous work may contribute to the field of study addressed in this article. Citing reputed authors strengthens the research's credibility, linking current findings to established scientific endeavors and reinforcing the significance of collaboration across studies.
12) Water:
Water is referenced regarding the context of solvent used in synthesis. It highlights discussions on eco-friendly practices in chemical processes, advocating for the use of less harmful methods while engaging with standard synthetic techniques, reflecting the growing emphasis on sustainability in chemistry.
13) Pada:
Pada is noted in the references to acknowledge contributions to the field of organic chemistry, showing the interconnection among various researchers. This emphasizes the collaborative nature of scientific inquiry, where discoveries build upon each other, ultimately advancing research methodologies and applications.
14) Sah:
Shah is another author referenced, highlighting the interconnectedness of research in the field of synthetic chemistry. His contributions may cover related findings and methodologies, providing a comprehensive understanding and contextual grounding to the current study on triazolopyrimidine derivatives.
15) Tai:
Thai is mentioned as a part of the referenced literature, indicating his work's relevance to the field. This underscores the collaborative nature of scientific research, where different studies and findings from various authors support the foundation and framework for ongoing experimental investigations.
16) Pur:
Poor yields are discussed in the article as a common issue in chemical syntheses, reflecting the challenges faced in laboratory work. Addressing the factors that affect yield is essential for improving synthetic protocols, ultimately aiming to enhance the efficiency and efficacy of pharmaceutical development.
Other Science Concepts:
Discover the significance of concepts within the article: ‘An efficient protocol for the synthesis of 1,2,4- triazolo[1,5-a]pyrimidines’. Further sources in the context of Science might help you critically compare this page with similair documents: