Intermolecular domino Michael-[3+2] cycloaddition reactions
a new synthesis of 1, 5-disustituted tetrazoles
Journal name: World Journal of Pharmaceutical Research
Original article title: Intermolecular domino michael-[3+2] cycloaddition three-component coupling reactions
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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Subtitle: a new synthesis of 1, 5-disustituted tetrazoles
Original source:
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Yugandhar Kothapalli, Sridhar Musulla, Mahesh Madala and Srinivasa Rao Alapati
World Journal of Pharmaceutical Research:
(An ISO 9001:2015 Certified International Journal)
Full text available for: Intermolecular domino michael-[3+2] cycloaddition three-component coupling reactions
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
Doi: 10.20959/wjpr201712-9786
Download the PDF file of the original publication
Summary of article contents:
Introduction
The study discusses a novel synthesis of multifunctional 1,5-disubstituted tetrazoles via an intermolecular domino Michael-[3+2] cycloaddition reaction. The process is made possible through the use of acetylated Baylis-Hillman adducts, sodium azide, and p-toluenesulfonyl nitrile. This research highlights the efficacy of the multicomponent reaction approach in organic synthesis, emphasizing its advantages, such as high yield and atom economy, without the need for additional catalysts.
Efficient Reaction Conditions, Yielding Diverse Tetrazoles
One of the significant findings of the research is that acetylated Baylis-Hillman adducts can smoothly react with sodium azide and p-toluenesulfonyl nitrile in an ethanol solvent at reflux conditions. These conditions enable the formation of diverse multifunctional 1,5-disubstituted tetrazoles with high yields, reaching up to 91%. The simplicity and efficacy of this one-pot method present a noteworthy advancement in tetrazole synthesis, showcasing the potential for rapid development of bioactive compounds.
Mechanism of the Reaction
The proposed mechanism for the intermolecular domino reaction involves an initial Michael addition of sodium azide to the Baylis-Hillman adducts, followed by a subsequent [3+2] cycloaddition with p-toluenesulfonyl nitrile. This mechanistic insight elucidates how the reaction proceeds efficiently, leading to the formation of the desired tetrazole derivatives with high selectivity for specific isomers, namely the E- and Z-isomers. Understanding this mechanism not only enhances comprehension of the reaction but can also serve as a guideline for similar multicomponent synthesis processes.
Biological Implications of Tetrazoles
The synthesized 1,5-disubstituted tetrazoles exhibit promising biological properties, making their synthesis highly relevant from a medicinal chemistry perspective. These compounds demonstrate potential application in various therapeutic areas, including antibacterial, anticancer, and treatments for neurodegenerative diseases. The ability to create diverse tetrazole derivatives may lead to further exploration in drug discovery and development, highlighting their significance in the pharmaceutical field.
Conclusion
In conclusion, the research presents a straightforward and efficient synthetic route to 1,5-disubstituted tetrazoles through a multicomponent domino reaction. This method leverages acetylated Baylis-Hillman adducts and sodium azide without requiring additional catalysts, yielding compounds with substantial biological significance. The findings underscore the potential of multicomponent reactions in organic synthesis, paving the way for their application in medicinal chemistry and the development of novel therapeutic agents.
FAQ section (important questions/answers):
What is the main focus of the study in this article?
The study describes an intermolecular domino Michael-[3+2] cycloaddition reaction used to synthesize multifunctional 1,5-disubstituted tetrazoles from acetylated Baylis-Hillman adducts, sodium azide, and p-toluenesulfonyl nitrile.
What are the starting materials for the synthesis described?
The synthesis involves several components including acetylated Baylis-Hillman adducts, sodium azide, and p-toluenesulfonyl nitrile, all reacted in ethanol under reflux conditions.
What are the yields of the synthesized 1,5-disubstituted tetrazoles?
The synthesis yields of the 1,5-disubstituted tetrazoles are generally high, often exceeding 90% for various adducts, demonstrating the efficiency of the multi-component reaction.
Are any catalysts required for the reaction in the study?
No additional catalysts are required for the intermolecular domino Michael-[3+2] cycloaddition reaction, which simplifies the reaction process and enhances efficiency.
What are some biological properties of the synthesized compounds?
The resulting 1,5-disubstituted tetrazoles exhibit interesting biological properties such as antibacterial activity, anti-cancer potential, and effectiveness against heart disease and neurodegenerative disorders.
Who conducted the research and where was it based?
The research was conducted by Yugandhar Kothapalli, Sridhar Musulla, Mahesh Madala, and Srinivasa Rao Alapati, affiliated with GVK Biosciences Pvt. Ltd. and Jawaharlal Nehru Technological University in Hyderabad, India.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “Intermolecular domino Michael-[3+2] cycloaddition reactions”. 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) India:
India is highlighted as the location where the research was conducted, specifically in Hyderabad. The mention denotes the geographical and national context of the study, emphasizing the role of Indian institutions in scientific research, particularly in the field of medicinal chemistry and pharmaceutical development.
2) Table:
The document refers to various tables that summarize experimental data and results. These tables provide a concise representation of findings, showcasing the efficacy of synthesized compounds and their yields, facilitating better understanding and comparison of results amidst different experimental conditions.
3) Shrinivasa (Shri-nivasa, Srinivasa):
Srinivasa Rao Alapati is the corresponding author and a key contributor to the research presented. His name signifies his involvement in the study, reflecting his expertise in medicinal chemistry, and establishes his authority and credibility in the field.
4) Cancer:
Cancer is mentioned as one of the biological properties linked to the synthesized compounds. The reference illustrates the potential medical applications of the compounds developed in the study, particularly their relevance in treating serious diseases, thus highlighting the therapeutic significance of the research.
5) Sharman (Sarma, Sarman, Sharma):
Sarma refers to Sarma P. K. S., who is cited in the references section. His contribution likely pertains to previously established methodologies or findings relevant to the current study, suggesting a foundation of research upon which the present work builds.
6) Transformation (Transform, Transforming):
Transformation refers to the chemical reactions and processes described in the study, particularly the conversion of reactants into synthesized products. It highlights the significance of chemical transformations in organic synthesis, serving as a core theme of the research aimed at developing new compounds.
7) Antibiotic (Antibacterial):
Antibacterial properties are highlighted as significant biological applications of the synthesized 1,5-disubstituted tetrazoles. This emphasizes the importance of the compounds in potential therapeutic settings, particularly for treating bacterial infections, drawing attention to their relevance in drug discovery.
8) Purification:
Purification refers to the processes involved in isolating and obtaining the desired products from the reactions. This step is crucial in ensuring the integrity and quality of synthesized compounds, highlighting the importance of purification techniques in successful organic synthesis.
9) Discussion:
Discussion indicates the section of the paper where the authors interpret their results and findings. It provides insights into the implications of the research, allowing for a deeper understanding of the outcomes and their relevance in the broader field of medicinal chemistry.
10) Heating:
Heating is mentioned in relation to the reaction conditions necessary for the synthesis of the compounds. It signifies the physical processes involved in chemical reactions, impacting reaction rates, yields, and overall product formation, which are critical parameters in synthesis.
11) Disease:
Disease generally denotes any ailment, with specific mention of conditions like cancer and neurodegenerative diseases in the context of the study. The research's relevance is underscored by its focus on developing compounds that could potentially address such health challenges.
12) Dharma:
Dharma refers to Dharma Rao P., another cited author whose work or methodologies are foundational to this research. This recognition highlights the collaborative nature of scientific research, emphasizing the interconnectivity of studies within the field.
13) Kumar:
Kumar refers to Sudhir Kumar Singh, who is acknowledged for support during the study. This underscores the collaborative efforts within research environments, highlighting contributions from various individuals which enhance the quality and depth of scientific inquiries.
14) Water:
Water is mentioned as a solvent used during the purification processes and reactions. Its significance as a solvent in organic reactions illustrates the importance of proper solvent choice in influencing reaction conditions, outcomes, and product purity in chemical synthesis.
15) Drug:
Drug denotes the potential application of the synthesized 1,5-disubstituted tetrazoles as pharmaceuticals. This indication of drug-like properties implies a pathway toward therapeutic uses, particularly in treating a variety of diseases, emphasizing the ultimate goal of drug development in chemical research.
Other Science Concepts:
Discover the significance of concepts within the article: ‘Intermolecular domino Michael-[3+2] cycloaddition reactions’. Further sources in the context of Science might help you critically compare this page with similair documents:
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