Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles
| Autor: | Carlos Kleber Z. Andrade, Angélica de Fátima S. Barreto, Veronica Alves dos Santos |
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| Rok vydání: | 2017 |
| Předmět: |
consecutive Ugi reactions
Isocyanide Sequence (biology) 010402 general chemistry 01 natural sciences Full Research Paper law.invention lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry law Molecule lcsh:Science Ugi-azide reaction Bearing (mechanical) 010405 organic chemistry Organic Chemistry 1 5-disubstituted tetrazoles Combinatorial chemistry 0104 chemical sciences Chemistry chemistry isocyanide-based multicomponent reactions (IMCRs) lcsh:Q Azide acylhydrazines |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 13, Iss 1, Pp 2596-2602 (2017) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.13.256 |
| Popis: | Isocyanide-based multicomponent reactions (IMCRs) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Our strategy was accomplished in only three steps: first, a one-pot hydrazino-Ugi-azide four-component reaction; second a hydrazinolysis and finally an additional hydrazino-Ugi-azide reaction. This sequence provides the title compounds in moderate to excellent yields. The products synthesized herein contain functional groups within their structures that can be easily modified to obtain new acylhydrazino 1,5-disubstituted tetrazoles. |
| Databáze: | OpenAIRE |
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