- Chemoselective reductive alkylation of ammonia with carbonyl compounds: Synthesis of primary and symmetrical secondary amines
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An efficient, general procedure for highly chemoselective reductive mono-alkylation of ammonia with ketones is reported. Treatment of ketones with ammonia in ethanol and titanium(IV) isopropoxide, followed by in situ sodium borohydride reduction, and a straightforward workup afforded primary amines in good to excellent yields. Reductive alkylation of ammonia with aldehydes, on the other hand, afforded the corresponding symmetrical secondary amines selectively.
- Miriyala, Bruhaspathy,Bhattacharyya, Sukanta,Williamson, John S.
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p. 1463 - 1471
(2007/10/03)
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- Tetracyclic benzimidazole derivatives and combinatorial libraries thereof
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The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.
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- 2-aminobenzoxazole derivatives and combinatorial libraries thereof
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The present invention relates to novel 2-aminobenzoxazole derivative compounds of the following formula: wherein R1 to R4 and Z have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminobenzoxazole derivative compounds.
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- Selective monoalkylation of ammonia: A high throughput synthesis of primary amines
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Primary amines are obtained in good to excellent yields by highly selective monoalkylation of ammonia with alkyl and aryl ketones using titanium(IV) isopropoxide and sodium borohydride.
- Bhattacharyya, Sukanta,Neidigh, Kurt A.,Avery, Mitchell A.,Williamson, John S.
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p. 1781 - 1783
(2007/10/03)
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- Method for synthesizing 2-substituted imidazoles
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The present invention is a method of preparing 2-substituted imidazoles from readily available imidazoles having a leaving group in the 2-position, by alkylating the imidazole under mild conditions to afford a 3-N-alkylated imidazolium salt; and coupling the imidazolium salt with a nucleophile also under mild conditions to afford a 2-substituted 3-N-alkylated imidazolium salt. The reaction product can optionally be isolated and purified. The 2-substituted 3-N-alkylated imidazolium salt is hydrolyzed to afford a 2-substituted imidazole. Alternatively, the imidazole is coupled with a nucleophile in the presence of fluoride ion to provide a 2-substituted imidazole.
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