Facile conversion of pyridine propargylic alcohols to enones stereochemistry of protonation of allenol
Yazarlar (2)
Prof. Dr. Ramazan ERENLER Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Jean François Biellmann Academia Sinica, Institute of Chemistry, Tayvan
| Makale Türü | Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale) | ||
| Dergi Adı | Tetrahedron Letters (Q2) | ||
| Dergi ISSN | 0040-4039 Dergi Bilgileri (2005) | ||
| Dergi Tarandığı Indeksler | SCI-Expanded | ||
| Makale Dili | İngilizce | Basım Tarihi | 08-2005 |
| Kabul Tarihi | – | Yayınlanma Tarihi | 01-08-2005 |
| Cilt / Sayı / Sayfa | 46 / 34 / 5683–5685 | DOI | 10.1016/j.tetlet.2005.06.087 |
| Makale Linki | http://linkinghub.elsevier.com/retrieve/pii/S0040403905013419 | ||
| UAK Araştırma Alanları |
Organik Kimya
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| Özet |
| The conversion of 4-pyridyl propargylic alcohols 1 to the (E)-propenones 3 and propynones 2 occurs under mild reaction conditions, pyridinium chloride in methanol at room temperature. (Z)-4-Pyridyl propenones 11 are detected as initial products when large substituents such as trimethylsilyl, tert-butyl and phenyl are attached at C-3 of the propynols and these (Z)-enones 11 are isomerised to the (E)-isomers 3 under the reaction conditions. In the presence of deuterated solvent, both hydrogens at the double bond of enone 3d are deuterated. An allenol is proposed as intermediate whose preferential protonation occurs at the less hindered side giving the (Z)-enone. The propargylic alcohols, pyridin-2-yl 12 and quinolin-4-yl 5, are converted to (E)-enones 13 and 7, respectively. |
| Anahtar Kelimeler |
| Enone | Heterocyclic | Isomerisation | Propargylic alcohol | Pyridinium chloride | Ynone |
Science Direct
Facile conversion of pyridine propargylic alcohols to enones stereochemistry of protonation of allenol
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| Yöksis | 3 |
| Web of Science | 15 |
| Scopus | 21 |
| Google Scholar | 29 |