Synthesis of New Bis‐imidazole Derivatives |
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| Authors: | Marcin Jasiński Grzegorz Mlostoń Paulina Mucha Anthony Linden Heinz Heimgartner |
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| Institution: | 1. University of ?ód?, Department of Organic and Applied Chemistry, Narutowicza 68, PL‐90‐136 ?ód?, (phone: +48?42?635?5761;2. fax: +48?42?635?5380);3. Part of the planned Ph.D. thesis of M. J., University of ?ód?.;4. Part of the planned Ph.D. thesis of P.M., University of ?ód?.;5. Organisch‐chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone: +41?44?635?4282;6. fax: +41?44?635?6812) |
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| Abstract: | The reaction of aldimines with α‐(hydroxyimino) ketones of type 10 (1,2‐diketone monooximes) was used to prepare 2‐unsubstituted imidazole 3‐oxides 11 bearing an alkanol chain at N(1) (Scheme 2, Table 1). These products were transformed into the corresponding 2H‐imidazol‐2‐ones 13 and 2H‐imidazole‐2‐thiones 14 by treatment with Ac2O and 2,2,4,4‐tetramethylcyclobutane‐1,3‐dithione, respectively (Scheme 3). The three‐component reaction of 10 , formaldehyde, and an alkane‐1,ω‐diamine 15 gave the bis1H‐imidazole 3‐oxides] 16 (Scheme 4, Table 2). With Ac2O, 2,2,4,4‐tetramethylcyclobutane‐1,3‐dithione or Raney‐Ni, the latter reacted to give the corresponding bis2H‐imidazol‐2‐ones] 19 and 20 , bis2H‐imidazol‐2‐thione] 21 , and bisimidazole] 22 , respectively (Schemes 5 and 6). The structures of 11a and 16b were established by X‐ray crystallography. |
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| Keywords: | Imidazole 3‐oxides 2H‐Imidazol‐2‐ones 1 3‐dihydro‐ 2H‐Imidazole‐2‐thiones 1 3‐dihydro‐ Bis‐imidazoles X‐Ray crystallography |
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