Home Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines
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Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines

  • H. Möhrle and M. Jeandrée
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 55 Issue 1

Dehydrogenation of 2-(1-piperidinyl)-benzaldehydes 1-3 using mercury(II)-EDTA gen­ erated the lactams 4-6, indicating a reversible reaction of a carbinolamine intermediate with the formyl group. The yields and oxidation rates decreased by 4-substitution in the piperidine moiety.

The 2-(1-piperidinyl)-acetophenones 11, 16-19 showed a similar behavior with mercury(II)-EDTA but gave rise to a product pattern. The trans-benzoquinolizidones 12, 20, 23, 26, 29 resulted from the cyclic iminium compounds reacting with the acetyl group as nucleophile. By another oxidation these species were partially transformed to the quinolinones 13, 21, 24, 27, 30. An intermediate electrophilic neighboring of the carbonyl group with the cyclic hemiaminals led finally to the lactams 14, 22, 25, 28, 31. Mechanisms for the reactions are proposed

: Benzoquinolizidone; Quinolone; N-Arylpiperidone; Neighboring Group Participation. Mercury(II)-EDTA Dehydrogenation
Received: 1999-10-26
Published Online: 2014-6-2
Published in Print: 2000-1-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Masthead
  2. Contents
  3. Alkylsubstituierte Cyclopentadienylvanadium(V)-Komplexe: tC4H9N=VCpRCl2 / Alkylated Cyclopentadienylvanadium (V) Complexes: tC4H9N =VCpRC l2
  4. A Comparison of the Enamino Carbonyl Conjugation Efficiency for Hydrogen Bonding Formation in Pyridone and Dihydropyridone Systems
  5. peri-Interactions in Naphthalenes, 3 [1]. On Hypercoordination in 8-Dimethylamino-naphth-1-yl-phosphonium salts and -phosphines
  6. Untersuchungen zur Thermolyse von Si2OCl6 / Thermolysis of Si2OCl6
  7. Chemischer Transport fester Lösungen am Beispiel von Mischspineilen / Chemical Transport of Solid Solutions: Mixed Spinels
  8. Phenylmercury Chloride: Its Single-Crystal X-Ray Structure and Some Aspects of its Biological Chemistry
  9. Preparation and Crystal Structure of Na4TiSe4. A Selenotitanate with Discrete Tetrahedral Anions
  10. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von (Ph3PNPPh3)[OsF5Cl]·CH2Cl2 und cis-(Ph3PNPPh3)[OsF4Cl2]·CH2Cl2 / Crystal Structures, Vibrational Spectra and Normal Coordinate Analysis of (Ph3PNPPh3) [OsF5Cl]·CH2Cl2 and cis-(Ph3PNPPh3 )[OsF4Cl2]·CH2Cl2
  11. Synthese, Struktur und Reaktivität von Aminomethylpyridin- zinkdihalogeniden / Synthesis, Structure and Reactivity of Aminomethylpyridine Zinc Dihalides
  12. Singly Charged λ6Si-Silicate Anions with an SiF5C Skeleton: Syntheses and Crystal Structure Analyses of the Ionic Hexacoordinate Silicon Compounds [Me3NH][F5SiCH2NMe2H]·H2O and [Me3NH][F5SiCH2NMe2H]·H2O
  13. Thermische Zersetzung und Lösungskalorimetrie von Ammoniumneodymiodiden / Thermal Decomposition and Solution Calorimetry of Ammonium Neodymium Iodides
  14. Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines
  15. Catalytic Oxidation of a Trialkyl-Substituted Phenol and Aniline with Biomimetic Schiff Base Complexes
  16. 2-Hexanoyl-1-tribromomethyl-1,2,3,4-tetrahydro-β-carboline: Crystal Structure Analysis of a Potent Inhibitor of Complex I of Mitochondrial Respiration
  17. Chemical Constituents of Ajuga parviflora
  18. Amino Acid Derivatives in Organic Synthesis, Part 4 [1]: Facile Synthesis of Heterocycles Containing a Glycine Residue
  19. Di-tert-alkyl Nitroxyl Radicals. Synthesis, Physical Properties and Applications as Inhibitors of Vinyl Polmerization at Elevated Temperatures
  20. A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
https://doi.org/10.1515/znb-2000-0113

Articles in the same Issue

  1. Masthead
  2. Contents
  3. Alkylsubstituierte Cyclopentadienylvanadium(V)-Komplexe: tC4H9N=VCpRCl2 / Alkylated Cyclopentadienylvanadium (V) Complexes: tC4H9N =VCpRC l2
  4. A Comparison of the Enamino Carbonyl Conjugation Efficiency for Hydrogen Bonding Formation in Pyridone and Dihydropyridone Systems
  5. peri-Interactions in Naphthalenes, 3 [1]. On Hypercoordination in 8-Dimethylamino-naphth-1-yl-phosphonium salts and -phosphines
  6. Untersuchungen zur Thermolyse von Si2OCl6 / Thermolysis of Si2OCl6
  7. Chemischer Transport fester Lösungen am Beispiel von Mischspineilen / Chemical Transport of Solid Solutions: Mixed Spinels
  8. Phenylmercury Chloride: Its Single-Crystal X-Ray Structure and Some Aspects of its Biological Chemistry
  9. Preparation and Crystal Structure of Na4TiSe4. A Selenotitanate with Discrete Tetrahedral Anions
  10. Kristallstrukturen, Schwingungsspektren und Normalkoordinatenanalyse von (Ph3PNPPh3)[OsF5Cl]·CH2Cl2 und cis-(Ph3PNPPh3)[OsF4Cl2]·CH2Cl2 / Crystal Structures, Vibrational Spectra and Normal Coordinate Analysis of (Ph3PNPPh3) [OsF5Cl]·CH2Cl2 and cis-(Ph3PNPPh3 )[OsF4Cl2]·CH2Cl2
  11. Synthese, Struktur und Reaktivität von Aminomethylpyridin- zinkdihalogeniden / Synthesis, Structure and Reactivity of Aminomethylpyridine Zinc Dihalides
  12. Singly Charged λ6Si-Silicate Anions with an SiF5C Skeleton: Syntheses and Crystal Structure Analyses of the Ionic Hexacoordinate Silicon Compounds [Me3NH][F5SiCH2NMe2H]·H2O and [Me3NH][F5SiCH2NMe2H]·H2O
  13. Thermische Zersetzung und Lösungskalorimetrie von Ammoniumneodymiodiden / Thermal Decomposition and Solution Calorimetry of Ammonium Neodymium Iodides
  14. Reaktionsbeteiligung elektrophiler Funktionen bei der Dehydrierung 4-substituierter Piperidine / Participation of Electrophilic Groups with the Dehydrogenation of 4-Substituted Piperidines
  15. Catalytic Oxidation of a Trialkyl-Substituted Phenol and Aniline with Biomimetic Schiff Base Complexes
  16. 2-Hexanoyl-1-tribromomethyl-1,2,3,4-tetrahydro-β-carboline: Crystal Structure Analysis of a Potent Inhibitor of Complex I of Mitochondrial Respiration
  17. Chemical Constituents of Ajuga parviflora
  18. Amino Acid Derivatives in Organic Synthesis, Part 4 [1]: Facile Synthesis of Heterocycles Containing a Glycine Residue
  19. Di-tert-alkyl Nitroxyl Radicals. Synthesis, Physical Properties and Applications as Inhibitors of Vinyl Polmerization at Elevated Temperatures
  20. A Novel Synthesis of Sulfone Systems as Antimicrobial Agents
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