Title:
METHOD FOR SYNTHESIS OF NITROXYL RADICAL
Document Type and Number:
WIPO Patent Application WO/2008/093881
Kind Code:
A1
Abstract:
Disclosed is a method for producing a nitroxyl radical derivative which can cause the substitution at position-2 and position-6 in a TEMPO compound readily and has high versatility. Also disclosed is a method for producing a nitroxyl radical derivative having a nitrogen nucleus labeled with 15N. Specifically, a triacetoneamine derivative is reacted with a ketone or an aldehyde in the presence of an ammonium salt or a 15N-labeled form thereof, thereby producing a 2,6-substituted-4-piperidone derivative.
Inventors:
UTSUMI HIDEO (JP)
SAKAI KIYOSHI (JP)
YAMADA KENICHI (JP)
SAKAI KIYOSHI (JP)
YAMADA KENICHI (JP)
Application Number:
PCT/JP2008/051899
Publication Date:
August 07, 2008
Filing Date:
January 30, 2008
Export Citation:
Assignee:
UNIV KYUSHU NAT UNIV CORP (JP)
UTSUMI HIDEO (JP)
SAKAI KIYOSHI (JP)
YAMADA KENICHI (JP)
UTSUMI HIDEO (JP)
SAKAI KIYOSHI (JP)
YAMADA KENICHI (JP)
International Classes:
C07D211/74; C07D211/94; C07D221/20; C07D491/20; C07D495/20; A61K51/00
Foreign References:
| JPS5010281B1 | 1975-04-19 | |||
| JPS471627B1 | ||||
| JPS4412414B1 | ||||
| JPS4631733B1 |
Other References:
MIURA Y. ET AL.: "Living' radical polymerization of styrene mediated by spiro ring-substituted piperidinyl-N-oxyl radicals. The effect of the spiro rings on the control of polymerization", POLYMER, vol. 44, no. 18, 2003, pages 5187 - 5194, XP004441838
YOSHIOKA T. ET AL.: "Studies on stable free radicals. VIII. The synthesis and oxidation of hindered 4-oxopiperidine derivatives", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 45, no. 2, 1972, pages 636 - 638, XP002493103
MIURA Y. ET AL.: "Low-Temperature "Living" Radical Polymerization of Styrene in the Presence of Nitroxides with Spiro Structures", MACROMOLECULES, vol. 34, no. 3, 2001, pages 447 - 455, XP008112466
WILEN C.-E. ET AL.: "Synthesis of Novel Hindered Amine Light Stabilizers (HALS) and Their Copolymerization with Ethylene or Propylene over Both Soluble and Supported Metallocene Catalyst Systems", MACROMOLECULES, vol. 33, no. 14, 2000, pages 5011 - 5026, XP001065167
MA Z. ET AL.: "Oxoammonium salts. 5. A new synthesis of hindered piperidines leading to unsymmetrical TEMPO-type nitroxides. Synthesis and enantioselective oxidations with chiral nitroxides and chiral oxoammonium salts", J. ORG. CHEM., vol. 58, no. 18, 1993, pages 4837 - 4843, XP008112467
WETTER C. ET AL.: "Steric and electronic effects in cyclic alkoxyamines - Synthesis and applications as regulators for controlled/living radical polymerization", CHEMISTRY - EUROPEAN JOURNAL, vol. 10, no. 5, 2004, pages 1156 - 1166, XP008112505
JOCKUSCH S. ET AL.: "Time Resolved CW-EPR Spectroscopy of Powdered Samples: Electron Spin Polarization of a Nitroxyl Radical Adsorbed on NaY Zeolite, Generated by the Quenching of Excited Triplet Ketones", J. PHYS. CHEM. B, vol. 105, no. 31, 2001, pages 7477 - 7481, XP008112468
H. UTSUMI ET AL., PNAS, vol. 103, 2006, pages 1463
Y MIURA; N. NAKAMURA; I. TANIGUCHI, MACROMOLECULES, vol. 34, 2001, pages 447
C. WETTER ET AL., CHEM. EUR. J., vol. 10, 2004, pages 1156
TAKESHITA ET AL., BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1573, 2002, pages 156 - 164
COUET, W R., TETRAHEDRON, vol. 41, no. 7, 1985, pages 1165 - 1172
FINKELSTEIN, E., BIOCHIMICA ET BIOPHYSICA ACTA, vol. 802, 1984, pages 90 - 98
See also references of EP 2128135A4
YOSHIOKA T. ET AL.: "Studies on stable free radicals. VIII. The synthesis and oxidation of hindered 4-oxopiperidine derivatives", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 45, no. 2, 1972, pages 636 - 638, XP002493103
MIURA Y. ET AL.: "Low-Temperature "Living" Radical Polymerization of Styrene in the Presence of Nitroxides with Spiro Structures", MACROMOLECULES, vol. 34, no. 3, 2001, pages 447 - 455, XP008112466
WILEN C.-E. ET AL.: "Synthesis of Novel Hindered Amine Light Stabilizers (HALS) and Their Copolymerization with Ethylene or Propylene over Both Soluble and Supported Metallocene Catalyst Systems", MACROMOLECULES, vol. 33, no. 14, 2000, pages 5011 - 5026, XP001065167
MA Z. ET AL.: "Oxoammonium salts. 5. A new synthesis of hindered piperidines leading to unsymmetrical TEMPO-type nitroxides. Synthesis and enantioselective oxidations with chiral nitroxides and chiral oxoammonium salts", J. ORG. CHEM., vol. 58, no. 18, 1993, pages 4837 - 4843, XP008112467
WETTER C. ET AL.: "Steric and electronic effects in cyclic alkoxyamines - Synthesis and applications as regulators for controlled/living radical polymerization", CHEMISTRY - EUROPEAN JOURNAL, vol. 10, no. 5, 2004, pages 1156 - 1166, XP008112505
JOCKUSCH S. ET AL.: "Time Resolved CW-EPR Spectroscopy of Powdered Samples: Electron Spin Polarization of a Nitroxyl Radical Adsorbed on NaY Zeolite, Generated by the Quenching of Excited Triplet Ketones", J. PHYS. CHEM. B, vol. 105, no. 31, 2001, pages 7477 - 7481, XP008112468
H. UTSUMI ET AL., PNAS, vol. 103, 2006, pages 1463
Y MIURA; N. NAKAMURA; I. TANIGUCHI, MACROMOLECULES, vol. 34, 2001, pages 447
C. WETTER ET AL., CHEM. EUR. J., vol. 10, 2004, pages 1156
TAKESHITA ET AL., BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1573, 2002, pages 156 - 164
COUET, W R., TETRAHEDRON, vol. 41, no. 7, 1985, pages 1165 - 1172
FINKELSTEIN, E., BIOCHIMICA ET BIOPHYSICA ACTA, vol. 802, 1984, pages 90 - 98
See also references of EP 2128135A4
Attorney, Agent or Firm:
KOBAYASHI, Hiroshi et al. (IKUBO & KATAYAMA Fukuoka Bldg. 9th Fl.,8-7, Yaesu 2-chome, Chuo-k, Tokyo 28, JP)
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