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http://hdl.handle.net/11452/26444
Başlık: | Synthesis and reactivity of tetrahydroimidazo [1,5-b][1,2,4]oxadiazol-2(1H)-thiones |
Yazarlar: | Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü. Coşkun, Necdet Tat, Fatma Tirli 7004177880 7801421136 |
Anahtar kelimeler: | Chemistry Engineering Imidazoline 3-oxides 1,3-dipolar cycloaddition Tetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1H)-thiones 4H-[1,2,4]oxadiazole-5-thione 1,3-dipolar cycloaddition Imidazoline 3-oxides Diastereoselective addition Regio Nitrones |
Yayın Tarihi: | 2004 |
Yayıncı: | TÜBİTAK |
Atıf: | Coşkun, N. ve Tat, F. T. (2004). “Synthesis and reactivity of tetrahydroimidazo [1,5-b][1,2,4]oxadiazol-2(1H)-thiones”. Turkish Journal of Chemistry, 28(1), 1-7. |
Özet: | 1,3-Dipolar cycloaddition of imidazoline 3-oxides I with methylisothiocyanate proceeds regio- and diastereoselectively to give tetrahydroimidazo[1,5-b][1,2,4]oxadiazol-2(1H)-thiones 3 in high yields. The cis configuration of the adducts was proved by our double cis elimination test as well as by NOESY experiments. Adducts 3a-c undergo ring opening at reflux in acetonitrile to give imidazoles while 3d-e undergo retro dipolar cycloaddition to give the starting nitrones 1d-e. The imidazooxadiazol-2-thiones 3a-e were treated with concentrated HCl in ethanol at 50degreesC to give the corresponding 4H-[1,2,4]oxadiazole-5-thione only in cases in which the substituent at C-6 is an aryl. |
URI: | https://dctubitak.researchcommons.org/chem/vol28/iss1/1/ http://hdl.handle.net/11452/26444 |
ISSN: | 1300-0527 |
Koleksiyonlarda Görünür: | Scopus TrDizin Web of Science |
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