- Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium
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The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.
- Daw, Prosenjit,Ben-David, Yehoshoa,Milstein, David
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supporting information
p. 11931 - 11934
(2018/09/27)
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- Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation
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A straightforward and solventless synthesis of pyrroles was developed by using mechanochemical activation and a biosourced organic acid as the catalyst. Relative to traditional Paal-Knorr methodologies, various N-substituted pyrroles were obtained in very short reaction times. By reaction with unreactive diketones, desymmetrized aliphatic and aromatic compounds were also synthesized.
- Akelis, Liudvikas,Rousseau, Jolanta,Juskenas, Robertas,Dodonova, Jelena,Rousseau, Cyril,Menuel, Stphane,Prevost, Dominique,Tumkeviius, Sigitas,Monflier, Eric,Hapiot, Frdric
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- Sulfamic acid as efficient and reusable catalytic system for the synthesis of pyrrole, furan, and thiophene derivatives
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Sulfamic acid has been utilized for the first time as an efficient and reusable catalytic system for the synthesis of heteroaromatics such as pyrrole, furan, and thiophene derivatives from 1,4-diketones. This new procedure offers significant improvements in the reaction rates and yields in a shorter reaction time and a lower reaction temperature contrasted with the reported results. The recovered catalyst can be reused for subsequent runs with only a gradual decrease in activity. The most important feature is that the reaction process is homogeneous whereas the separation process is heterogeneous, which is often seen in other catalysts, and so it is a good character for technical application.
- Luo, Haitang,Kang, Yuru,Li, Qi,Yang, Liming
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p. 144 - 148
(2008/09/18)
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- Simple, efficient and convenient synthesis of pyrroles and pyrazoles using zeolites
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A convenient heterogeneous catalytic methodology for the synthesis of Pyrroles and Pyrazoles by an intermolecular reaction of γ or β-diketones with primary amines or hydrazine derivatives over zeolites are described.
- Sreekumar,Padmakumar, Raghavakaimal
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p. 1661 - 1665
(2007/10/03)
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- Pyrrole and Pyrazole Ring Closure in Heterogeneous Media
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Pyrroles and pyrazoles may be conveniently prepared by dispersing primary amines or hydrazines and 1,4- or 1,3-diketones, respectively, on alumina or clay (montmorillonite K 10) without solvent, keeping the mixture at 20 deg C or higher temperatures for 1-26 h, and then eluting the product with dichloromethane.
- Texier-Boullet, F.,Klein, B.,Hamelin, J.
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p. 409 - 411
(2007/10/02)
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- AN H-1, C-13 AND N-15 NMR STUDY OF THE PAAL-KNORR CONDENSATION OF ACETONYLACETONE WITH PRIMARY AMINES
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The reaction of primary amines with acetonylacetone is shown by H-1, C-13 and N-15 NMR spectroscopy to proceed to the N-substituted -2,5-dimethylpyrroles via the intermediacy of N-substituted imines.Increased steric hindrance reduces rates of imine formation and decay.
- Katritzky, Alan R.,Yousaf, Taher I.,Chen, Ban Chi,Guang-Zhi, Zeng
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p. 623 - 628
(2007/10/02)
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