Application of intramolecular 1,3-dipolar cyclic addition of azide and olefin; construction of (pyrrolidine-2-ylidene)glycinate and glycinamides
| Autor: | Souichi Monma, Masataka Sakayanagi, Noriko Satou, Takahiro Satou, Yoshihiro Harigaya, Kazuyoshi Takeda, Keiko Asano, Yaeko Konda-Yamada |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
chemistry.chemical_classification
Olefin fiber Addition reaction Azides Pyrrolidines Glycine General Chemistry General Medicine Carzinophilin Alkenes Medicinal chemistry Pyrrole derivatives Pyrrolidine Amino acid chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Organic chemistry Azide |
| Zdroj: | Chemicalpharmaceutical bulletin. 53(5) |
| ISSN: | 0009-2363 |
| Popis: | Oxopropyl E-(pyrrolidine-2-ylidene)glycinamide (5c) and allyl E-(pyrrolidine-2-ylidene)glycinate (5d) were effectively synthesized from 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl(TBDMS)-D-arabinal (7) using intramolecular 1,3-dipolar cyclic reaction of azide and olefin as a key reaction. These results proved this cyclic reaction should be applicable for the synthesis of various (pyrrolidine-2-ylidene)glycinate and glycinamide. In addition, the development of a synthetic route for the precursor of an unsaturated cyclic dehydro amino acid involved in azinomycins (carzinophilin) using relating glycinate, methyl E-(pyrrolidine-2-ylidene)glycinate (5a) was described. |
| Databáze: | OpenAIRE |
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