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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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