Please use this identifier to cite or link to this item:
http://hdl.handle.net/10773/20280| Title: | Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles |
| Author: | Talhi, Oualid Pinto, Diana C. G. A. Almeida Paz, Filipe A. Hamdi, Maamar Silva, Artur M. S. |
| Keywords: | spiro bisheterocycles oxygen and nitrogen heterocycles bisnucleophiles NMR X-ray diffraction |
| Issue Date: | 2015 |
| Publisher: | GEORG THIEME VERLAG KG |
| Abstract: | A facile and rapid access to bridgehead oxygen-and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in optimal yields (42-71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies. |
| Peer review: | yes |
| URI: | http://hdl.handle.net/10773/20280 |
| DOI: | 10.1055/s-0034-1379613 |
| ISSN: | 0936-5214 |
| Publisher Version: | 10.1055/s-0034-1379613 |
| Appears in Collections: | CICECO - Artigos |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles_10.1055s-0034-1379613.pdf | 411.12 kB | Adobe PDF | View/Open |
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