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α-Dicarbonylmonophenylhydrazone als Nucleophile und Nachbargruppen / α-Dicarbonylmonophenylhydrazones as Nucleophiles and Neighbouring Groups
-
Hans Möhrle
and
Georg Keller
Published/Copyright:
June 2, 2014
Abstract
The α-dicarbonylmonophenylhydrazones 1 and 8 do not react as simple ,,CH-acidic compounds“ in the Mannich condensation reaction. In a concerted reaction with aminals in absolute dioxane they give rise to the products 5a-e and 10a-e with better practicability and much higher yields compared with the conventional method. The formal Mannich bases 5a/5b/5d and 10a/10b/10d with a cyclic amine part show in the dehydrogenation, using mercury- EDTA , a neighbouring group participation of the phenylhydrazono moiety yielding the corresponding lactams. With 5c only cyclization occurs leading to 1,2,4-triazine 19 in low yield, while 10c shows no dehydrogenation but an amine elimination to the vinyl-azo com pound 21 with consecutive cycloaddition leading to the 1,2-diazine 23.
Received: 2001-3-14
Published Online: 2014-6-2
Published in Print: 2001-6-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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- Fluoreliminierung aus Graphitfluorid mit Magnesium / Defluorination of Graphite Fluoride Applying Magnesium Emst-Christian Koch
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- Synthesis and Solid-Phase Application of a 9-Xanthenyl Handle
- α-Dicarbonylmonophenylhydrazone als Nucleophile und Nachbargruppen / α-Dicarbonylmonophenylhydrazones as Nucleophiles and Neighbouring Groups
- Synthese und Eigenschaften von α Aminocarbohydroximsäure-estern / Synthesis and Properties of α-Aminocarbohydroximic Esters
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Keywords for this article
C-Aminomethylation;
Mercury(II)-EDTA Dehydrogenation;
Intramolecular Cyclization
Articles in the same Issue
- A One-Dimensional Polymeric Form of the Polycation Te82+ in the Structure of Te8[Bi4Cl14]
- Preparation and Structure of Cyclic Gallium(III) and Gallium(II) 2-Amino-ethyl-amides
- New Metal-Rich Compounds NblrSi, NblrGe, and TalrSi -Synthesis, Structure, and Magnetic Properties
- Wechselwirkungen in Molekülkristallen, 174 [1, 2]. Kristallzüchtung und Strukturbestimmung verschiedenartig Methyl-substituierter Imidodiphosphorsäuretetraphenylester / Interaction in Molecular Crystals, 174 [1, 2]. Crystal Growth and Structure Determination of Differently Methyl-Substituted Tetraphenyl Imidodiphosphates
- Wechselwirkungen in Molekülkristallen, 175 [1, 2]. Kristallzüchtung und Strukturbestimmung von {Cäsium-tetraphenylimido- diphosphat}-Aggregaten mit unterschiedlicher lipophiler Umhüllung durch verschiedenartig Methyl-substituierte Phenylringe sowie relativistische DFT-Modellberechnungen zu Cäsium/Cäsium-Wechselwirkungen / Interaction in M olecular Crystals, 175 [1,2]. Crystal Growth and Structure Determination of {Cesium-tetraphenylimidodiphosphate} Aggregates with Differing Lipophilic Wrapping Due to Differently Methyl-Substituted Phenyl Rings, and Relativistic DFT-Model Calculations of Cesium/Cesium Interactions
- Fluoreliminierung aus Graphitfluorid mit Magnesium / Defluorination of Graphite Fluoride Applying Magnesium Emst-Christian Koch
- Synthesis and Crystal Structure of a Novel Polymeric Lead(II) Complex with Thiosemicarbazonato and Thiocyanate Ligands
- Dependence of the Distortion of the Square Pyramids in N, N-Dimethylethylenediammonium Pentachloroantimonate(III) on the Geometry of Hydrogen Bonds
- Synthesis and Solid-Phase Application of a 9-Xanthenyl Handle
- α-Dicarbonylmonophenylhydrazone als Nucleophile und Nachbargruppen / α-Dicarbonylmonophenylhydrazones as Nucleophiles and Neighbouring Groups
- Synthese und Eigenschaften von α Aminocarbohydroximsäure-estern / Synthesis and Properties of α-Aminocarbohydroximic Esters
- A New Synthesis of Two Naturally Occurring Dihydrobenzo[b]furan-Type Neolignans of Potential Biological Activity
