- Selective sequential cross-coupling reactions on imidazole towards neurodazine and analogues
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Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.
- Recnik, Lisa-Maria,Abd El Hameid, Mohammed,Haider, Maximilian,Schnuerch, Michael,Mihovilovic, Marko D.
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p. 1387 - 1405
(2013/07/05)
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- Single-flask polyfunctionalization of the imidazole ring; a streamlined route to the antitumor agent carmethizole
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Three sequential treatments of an N-protected tribromoimidazole with n-BuLi/electrophile in a 1-pot process leads to N-protected 2,4,5-trisubstituted imidazoles. The method can be applied to the preparation of the immediate of carmethizole.
- Lipshutz, Bruce H.,Hagen, William
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p. 5865 - 5868
(2007/10/02)
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- Azoles. Part 4. Nucleophilic Substitution Reactions of Halogenoimidazoles
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A number of N-protected derivatives of 2,4,5-tribromoimidazole, 4(5)-bromo-5(4)-nitroimidazole, and 2,4(5)-dibromo-5(4)-nitroimidazole have been prepared by standard procedures and treated with various nucleophiles.Whereas 2,4,5-tribromo (and tri-iodo)imidazole reacted with sodium benzenethiolate to give the corresponding 4,5-dihalogenoimidazole and diphenyl disulphide, 1-protected derivatives of 2,4,5-tribromoimidazole reacted with various sodium alkane (or arene)thiolates and with sodium isopropoxide, in isoprpopyl alcohol, by displacement of the 2-bromine atom. 1-Benzyl-5-bromo-4-nitroimidazole (14), 2-(5-bromo-4-nitroimidazol-1-yl)acetate (25), and 5-bromo-4-nitro-1-phenacylimidazole (26) reacted by displacement of the 5-bromine atom.The product arising from reaction of the last compound with ethyl 2-mercaptoacetate in ethanol in the presence of base, cyclised to give ethyl 3-hydroxy-7-nitro-3-phenylimidazolothiazine-2-carboxylate (35).
- Iddon, Brian,Khan, Nazir,Lim, Bee Lan
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p. 1437 - 1444
(2007/10/02)
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- A Convenient Synthesis of Thienoimidazoles
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1-Protected and 1,2-diprotected derivatives of 4-bromoimidazole-5-carbaldehyde were prepared from imidazole via 2,4,5-tribromoimidazole and reacted with ethyl 2-mercaptoethanoate to give the title compounds.
- Iddon, Brian,Khan, Nazir,Lim, Bee Lam
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p. 1428 - 1429
(2007/10/02)
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