An Efficient Metal-Free Methodology for the Synthesis of Hydrazo-Linked 5-(4-aryl)-1H-1,2,4-Triazoles

IF 0.7 4区 化学 Q4 CHEMISTRY, ORGANIC Letters in Organic Chemistry Pub Date : 2024-08-28 DOI:10.2174/0115701786332586240819074232
Neha Rani, Deepak K. Aneja, Mayank Kinger, Rinku Soni, Monika Sihag, Sandeep Malik, Kirti Bhardwaj
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Abstract

Hydrazo compounds have displayed significant roles in both biological and physical aspects, such as spinamycin as a potent growth inhibitor against fungi and rat sarcoma cells, hydrazo tocopherol as a component of vitamin E, and electron-rich hydrazo-linked triazines as energetic materials. In this study, a metal-free approach was proposed for the synthesis of hydrazo-linked 5-(4- aryl)-1H-1,2,4-triazoles. The methods for the synthesis of 5-(4-aryl)-1H-1,2,4-triazoles initiated by the reaction of aldehyde with semicarbazide. The resulted compound, 5-(4-aryl)-1H-1,2,4-triazol-3- ol, upon reaction with phosphorous oxychloride yielded 3-chloro-5-(4-aryl)-1H-1,2,4-triazoles. These synthesized compounds upon fusión with various aryl and hetero aryl substituted hydrazines provided desired hydrazo moieties. Synthesized hydrazo compounds were characterized by spectroscopic techniques, viz. 1H-NMR, FT-IR and mass spectrometry. In this study, a series of novel hydrazo- linked 5-(4-aryl)-1H-1,2,4-triazoles were synthesized. The methodology proposed in this study eliminates the use of complicated procedures and heavy metals.
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合成 5-(4-芳基)-1H-1,2,4-三唑的高效无金属方法学
偶氮化合物在生物和物理两方面都发挥了重要作用,如作为真菌和大鼠肉瘤细胞强效生长抑制剂的旋光霉素、作为维生素 E 成分的生育酚偶氮,以及作为高能材料的富电子偶氮连接三嗪。本研究提出了一种无金属的方法来合成肼联 5-(4-芳基)-1H-1,2,4-三唑。合成 5-(4-芳基)-1H-1,2,4-三唑的方法始于醛与缩氨基脲的反应。得到的 5-(4-芳基)-1H-1,2,4-三唑-3-醇化合物与氧氯化磷反应后生成 3-氯-5-(4-芳基)-1H-1,2,4-三唑。这些合成化合物在与各种芳基和杂芳基取代的肼反应后,得到了所需的偶氮分子。合成的偶氮化合物通过光谱技术(即 1H-NMR、FT-IR 和质谱)进行表征。在本研究中,合成了一系列新颖的联氮 5-(4-芳基)-1H-1,2,4-三唑。本研究提出的方法无需使用复杂的程序和重金属。
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来源期刊
Letters in Organic Chemistry
Letters in Organic Chemistry 化学-有机化学
CiteScore
1.30
自引率
12.50%
发文量
135
审稿时长
7 months
期刊介绍: Aims & Scope Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts. The journal is an essential reading for all organic chemists belonging to both academia and industry.
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