Unprecedented cyclization of α-diazo hydrazones upon N-H functionalization: A Et3N base promoted one-step synthetic approach for the synthesis of N-amino-1,2,3-triazole derivatives from α-diazo hydrazone |
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Authors: | Bharath Kumar Kuruba Lourdusamy Emmanuvel Balasubramanian Sridhar Samuel Vasanthkumar |
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Institution: | 1. School of Science & Humanities, Department of Chemistry, Karunya University, India;2. Laboratory of X-ray Crystallography, CSIR – Indian Institute of Chemical Technology, Hyderabad, India |
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Abstract: | In this communication, for the first time, we are reporting α-diazo hydrazone synthesis from hydrazones derived from β-keto esters and 2,4-dinitro phenyl hydrazine via diazo transfer reaction. We also report an unexpected cyclization of the α-diazo hydrazones upon N-H functionalization to give highly functionalized N-amino-1,2,3-triazole derivatives under metal-free condition. This one-step synthetic protocol can serve as a general tool to access nitrogen rich 5- and 6-membered heterocycles in excellent yields. |
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Keywords: | Diazo esters 2 4-Dinitro phenyl hydrazones Metal-free reactions Triazole derivatives |
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