- Isoprene-catalyzed lithiation of imidazole: Synthesis of 2-(hydroxyalkyl)- and 2-(aminoalkyl)imidazoles
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2-Lithioimidazole was prepared by means of a new protocol, which consists of a slight excess of lithium metal in the presence of a substoichiometric amount of isoprene (20 mol%) in THF at room temperature. By reacting this organolithium with carbonyl elec
- Torregrosa, Rosario,Pastor, Isidro M.,Yus, Miguel
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p. 11148 - 11155
(2007/10/03)
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- The synthesis of 2-substituted azoles through a one-pot three-component reaction
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We have discovered a new reaction whereby 2-substituted azoles are formed in the reaction of an azolium ylide with reactive carbonyl compounds. These products contain a leaving group in the α-position, which on solvolysis in the presence of nucleophiles yield azoles with a variety of α-substituents. We have developed new aspects of this chemistry and expanded the scope to include imidazoles, thiazoles, benzimidazoles and triazoles, such that in two reaction steps a wide diversity of substitution patterns are obtained.
- Deng, Yijun,Hlasta, Dennis J.
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p. 189 - 192
(2007/10/03)
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- Synthesis and reactivities of 1,3-dimethyl-2-(α-hydroxy-benzyl)imidazolium and 1,3-dimethyl-2-(α-hydroxybenzyl)benzimidazolium iodides
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1,3-Dimethyl-2-(α-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazoline (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(α-hydroxybenzyl)imidazolium iodide (4a).
- Miyashita, Akira,Kurachi, Akihito,Matsuoka, Yoshiyuki,Tanabe, Noriko,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Higashino, Takeo
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p. 417 - 426
(2007/10/03)
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- Synthesis, Characterisation, and Reactivity of 1-(1-Methylimidazol-2-yl)ethenes
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Thermally labile 1-(1-methylimidazol-2-yl)ethenes, synthesised using the Wittig reaction, have been characterised as stable picrate or N-phenacyl salts.The free bases can be regenerated from the picrates on treatment with triethylamine and their reactivit
- Abarca-Gonzalez, Belen,Jones, R. Alan,Medio-Simon, Mercedes,Quilez-Pardo, Juan,Sepulveda-Arques, Jose,Zaballos-Garcia, Elena
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p. 321 - 331
(2007/10/02)
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