Unprecedented cyclization of α -diazo hydrazones upon N-H functionalization: A Et 3 N base promoted one-step synthetic approach for the synthesis of N-amino-1,2,3-triazole derivatives from α -diazo hydrazone
| Autor: | Samuel Vasanthkumar, Lourdusamy Emmanuvel, Bharath Kumar Kuruba, Balasubramanian Sridhar |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Phenyl hydrazine 1 2 3-Triazole Base (chemistry) 010405 organic chemistry Organic Chemistry Hydrazone One-Step 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Nitrogen rich chemistry Drug Discovery Surface modification Organic chemistry Diazo |
| Zdroj: | Tetrahedron. 73:2674-2681 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.03.061 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect