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α-Dicarbonylmonoxime als Nucleophile und Nachbargruppen / α-Dicarbonylmonoximes as Nucleophiles and Neighbour Groups

  • Hans Möhrle and Georg Keller
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 5

The α-dicarbonylmonooximes 1 and 11 do not react as simple “CH-acidic-compounds” in the Mannich condensation. In a concerted reaction with aminals in absolute dioxane they give rise to the products 4a - e and 12a - e with better practicability and much higher yields compared with the conventional method. The Mannich bases with a cyclic amine part show in the dehydrogenation, using mercury-EDTA, a neighbouring group participation of the oxime in type 4 and of the oxime or amide function in 12 yielding cyclized products. For the reaction a plausible mechanism is proposed.

Keywords : Aminal; C-Aminomethylation; Mercury(II)-EDTA Dehydrogenation; Intramolecular Cyclization
Received: 1999-1-27
Published Online: 2014-6-2
Published in Print: 1999-5-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Chemische Reaktionen in Salzschmelzen, XXI. Titan-vermittelte Synthese von Silanen in Chloroaluminat-Schmelzen / Chemical Reactions in Molten Salts, XXI. Titanium Mediated Synthesis of Silanes in Chloroaluminate Melts
  2. Hydrolytische Bildung von Perchlorsiloxanen / Formation of Chlorosiloxanes by Hydrolysis
  3. Umsetzung von Cyclopentadienylmetallcarbonylen mit Thionylhalogeniden - Neue Synthese halogenoverbrückter Cp*Co-Komplexe / Reaction of Cyclopentadienyl Metal Carbonyles with Thionylhalides - New Synthesis of Halogeno-Bridged Cp*Co Complexes
  4. Die Oxochlorovanadate PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN und (PPh4)2[VOCl4]·CH3CN mit auffälligen Abweichungen von der quadratisch-pyramidalen Anionenstruktur / The Oxochlorovanadates PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN and (PPh4)2[VOCl4]·CH3CN with Remarkable Deviations from the Square-Pyramidal Anion Structure
  5. S-, X-, Q- und W-Band-Pulver-EPR-Untersuchungen an Tetra-n -butylammonium-bis( 1,2-dicyanoethen-1,2-dithiolato)aurat(II), [(n-C4H9)4N]2[AuII(mnt)2] / S, X, Q and W Band Powder-EPR Investigations on Tetra-n-butylammoniumbis( 1,2-dicyanoethylene-1,2-dithiolato)aurate(II), [(n-C4H9)4N]2 [AuII(mnt)2]
  6. Unerwartete Reaktionsprodukte bei der Umsetzung von Mesitylmagnesiumbromid mit Arsentribromid / Unexpected Products from the Reaction of Mesitylmagnesium Bromide and Arsenic Tribromide
  7. 1.3.5-Triazin-2,4,6-trisulfenyltrichlorid: Synthese, Eigenschaften und Reaktionsverhalten / 1.3.5-Triazine-2,4,6-trisulfenyltrichloride: Synthesis, Properties and Reactions
  8. Verdampfungsverhalten von Lanthantrihalogeniden / Evaporation Behaviour of Lanthanum Trihalides
  9. Synthese und Molekülstruktur des [α-(Dichlormethylsilyl)ethyl]- dichlorboran-dimethylsulfid / Synthesis and Molecular Structure of [α-(Dichloromethylsilyl)ethyl]- dichloroborane-dimethylsulfide
  10. Organogallitimamide: Synthese und Kristallstrukturen von [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2 / Organogallium Amides: Synthesis and Crystal Structures of [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2
  11. α-Dicarbonylmonoxime als Nucleophile und Nachbargruppen / α-Dicarbonylmonoximes as Nucleophiles and Neighbour Groups
  12. Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides
  13. A Short and Productive Synthesis of Racemic α-Lipoic Acid
  14. A Short and Productive Synthesis of (R)-α-Lipoic Acid
  15. 5,10,15,20-Tetrakis(diphenylmethyl)porphyrin - A Nonplanar Porphyrin with Intermediate Degree of Ruffling
  16. Synthesis of 3-Amino(alkoxy)-2,4-dioxo-1,3-oxazolidine-5-carboxylates from Tartronic Esters
  17. Cyanothioacetamide and its Derivatives in Heterocyclic Synthesis: A New Route for the Synthesis of Several Pyridine and Thieno[2,3-b]pyridine Derivatives and their Biological Evaluation
  18. Synthese und Struktur von Prolinring-modifizierten Actinomycinen des X-Typs / Synthesis and Structure of Proline Ring Modified Actinomycins of the X-Type
  19. Neighbouring Group Participation of C-6 Substituents of Glucose Derivatives on the Stereoselectivity of the N-Glycosidic Linkage of Glycopeptides
  20. Synthese und Kristallstruktur von 3.6-Di-tert-butylpyridazin / Synthesis and Crystal Structure of 3.6-Di-tert-butylpyridazine
  21. p-Tolyl(trimethylsilylethynyl)sulfone as Synthon for the Synthesis of Cp(OC)2M-C =CSiMe3 (M ≡ Fe, Ru). Molecular Structure of Cp(OC)2Fe-C ≡ CSiMe3
https://doi.org/10.1515/znb-1999-0511
Keywords for this article
Aminal; C-Aminomethylation; Mercury(II)-EDTA Dehydrogenation; Intramolecular Cyclization

Articles in the same Issue

  1. Chemische Reaktionen in Salzschmelzen, XXI. Titan-vermittelte Synthese von Silanen in Chloroaluminat-Schmelzen / Chemical Reactions in Molten Salts, XXI. Titanium Mediated Synthesis of Silanes in Chloroaluminate Melts
  2. Hydrolytische Bildung von Perchlorsiloxanen / Formation of Chlorosiloxanes by Hydrolysis
  3. Umsetzung von Cyclopentadienylmetallcarbonylen mit Thionylhalogeniden - Neue Synthese halogenoverbrückter Cp*Co-Komplexe / Reaction of Cyclopentadienyl Metal Carbonyles with Thionylhalides - New Synthesis of Halogeno-Bridged Cp*Co Complexes
  4. Die Oxochlorovanadate PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN und (PPh4)2[VOCl4]·CH3CN mit auffälligen Abweichungen von der quadratisch-pyramidalen Anionenstruktur / The Oxochlorovanadates PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN and (PPh4)2[VOCl4]·CH3CN with Remarkable Deviations from the Square-Pyramidal Anion Structure
  5. S-, X-, Q- und W-Band-Pulver-EPR-Untersuchungen an Tetra-n -butylammonium-bis( 1,2-dicyanoethen-1,2-dithiolato)aurat(II), [(n-C4H9)4N]2[AuII(mnt)2] / S, X, Q and W Band Powder-EPR Investigations on Tetra-n-butylammoniumbis( 1,2-dicyanoethylene-1,2-dithiolato)aurate(II), [(n-C4H9)4N]2 [AuII(mnt)2]
  6. Unerwartete Reaktionsprodukte bei der Umsetzung von Mesitylmagnesiumbromid mit Arsentribromid / Unexpected Products from the Reaction of Mesitylmagnesium Bromide and Arsenic Tribromide
  7. 1.3.5-Triazin-2,4,6-trisulfenyltrichlorid: Synthese, Eigenschaften und Reaktionsverhalten / 1.3.5-Triazine-2,4,6-trisulfenyltrichloride: Synthesis, Properties and Reactions
  8. Verdampfungsverhalten von Lanthantrihalogeniden / Evaporation Behaviour of Lanthanum Trihalides
  9. Synthese und Molekülstruktur des [α-(Dichlormethylsilyl)ethyl]- dichlorboran-dimethylsulfid / Synthesis and Molecular Structure of [α-(Dichloromethylsilyl)ethyl]- dichloroborane-dimethylsulfide
  10. Organogallitimamide: Synthese und Kristallstrukturen von [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2 / Organogallium Amides: Synthesis and Crystal Structures of [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2
  11. α-Dicarbonylmonoxime als Nucleophile und Nachbargruppen / α-Dicarbonylmonoximes as Nucleophiles and Neighbour Groups
  12. Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides
  13. A Short and Productive Synthesis of Racemic α-Lipoic Acid
  14. A Short and Productive Synthesis of (R)-α-Lipoic Acid
  15. 5,10,15,20-Tetrakis(diphenylmethyl)porphyrin - A Nonplanar Porphyrin with Intermediate Degree of Ruffling
  16. Synthesis of 3-Amino(alkoxy)-2,4-dioxo-1,3-oxazolidine-5-carboxylates from Tartronic Esters
  17. Cyanothioacetamide and its Derivatives in Heterocyclic Synthesis: A New Route for the Synthesis of Several Pyridine and Thieno[2,3-b]pyridine Derivatives and their Biological Evaluation
  18. Synthese und Struktur von Prolinring-modifizierten Actinomycinen des X-Typs / Synthesis and Structure of Proline Ring Modified Actinomycins of the X-Type
  19. Neighbouring Group Participation of C-6 Substituents of Glucose Derivatives on the Stereoselectivity of the N-Glycosidic Linkage of Glycopeptides
  20. Synthese und Kristallstruktur von 3.6-Di-tert-butylpyridazin / Synthesis and Crystal Structure of 3.6-Di-tert-butylpyridazine
  21. p-Tolyl(trimethylsilylethynyl)sulfone as Synthon for the Synthesis of Cp(OC)2M-C =CSiMe3 (M ≡ Fe, Ru). Molecular Structure of Cp(OC)2Fe-C ≡ CSiMe3
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