Title:
METHOD FOR PRODUCING 2-AZAINDOLIZINE, METHOD FOR PRODUCING 2-AZAINDOLIZINE METAL COMPLEX, AND 2-AZAINDOLIZINE METAL COMPLEX
Document Type and Number:
WIPO Patent Application WO/2006/088028
Kind Code:
A1
Abstract:
Disclosed is a method for producing a 2-azaindolizine in a monomeric or dimeric form, or a metal complex thereof by a short process with high yield by using a reagent having less acridity and less toxicity. Also disclosed is a 2-azaindolizine metal complex in a monomeric or dimeric form as a novel compound which can be used for organic EL devices or the like. A 2-azaindolizine is produced by reducing a N-2-pyridylmethylcarbothioamide in the presence of an oxidizing agent. Then, a 2-azaindolizine metal complex is produced by reacting the 2-azaindolizine with a metal ion.
Inventors:
SHIBAHARA FUMITOSHI (JP)
MURAI TOSHIAKI (JP)
MURAI TOSHIAKI (JP)
Application Number:
PCT/JP2006/302557
Publication Date:
August 24, 2006
Filing Date:
February 14, 2006
Export Citation:
Assignee:
UNIV GIFU (JP)
SHIBAHARA FUMITOSHI (JP)
MURAI TOSHIAKI (JP)
SHIBAHARA FUMITOSHI (JP)
MURAI TOSHIAKI (JP)
International Classes:
C07D471/04; C07D519/00; C07F15/00; C09K11/06; G09F9/30; H01L27/32; H01L51/50; H01L51/54; C07B61/00
Domestic Patent References:
| WO2002044189A1 | 2002-06-06 |
Foreign References:
| JP2001035664A | 2001-02-09 | |||
| JP2001006877A | 2001-01-12 | |||
| JP2004168756A | 2004-06-17 | |||
| JP2003252888A | 2003-09-10 | |||
| JP2005044790A | 2005-02-17 | |||
| JP2002367785A | 2002-12-20 | |||
| JPS6143191A | 1986-03-01 |
Other References:
IRRGANG T. ET AL.: "Early and Late Transition Metal Complexes Stabilised by Imidazopyridazine-Substituted Bisamido Ligands", EUR. J. INORG. CHEM., 2005, pages 4382 - 4392, XP003000910
BLUHM M.E. ET AL.: "Complexes of Schiff Bases and Intermediates in the Copper-Catalyzed Oxidative Heterocyclization by Atmospheric Oxygen", INORGANIC CHEMISTRY, vol. 42, no. 26, 2003, pages 8878 - 8885, XP003000911
LIGTENBARG A.G. ET AL.: "Vanadium(v) complexes based on a bis(pyridine)-imine ligand (HL); synthesis and crystal structure of a dioxovanadium(v) complex involving a ligand cyclization", J. CHEM. SOC., DALTON TRANS., 1999, pages 659 - 661, XP001010414
ABUSHANAB E. ET AL.: "Imidazo[1,5-a]pyrazines. III. The Preparation and Chemistry of 3-(Phenylthiomethyl)imidazo[1,5-a]pyrazine (1,2)", J. HETEROCYCL. CHEM., vol. 12, no. 1, 1975, pages 207 - 209, XP003000913
GLOVER E.E. ET AL.: "Synthesis and Quaternization of Some Heterocyclic Mono- and Di-sulphides", J. CHEM. SOC., PERKIN TRANS, vol. 1, no. 21, 1973, pages 2595 - 2599, XP003000914
EL KHADEM H.S. ET AL.: "SYNTHESIS AND REARRANGEMENTS OF IMIDAZOLO- AND TRIAZOLO-DIAZINES", HETEROCYCLES, vol. 28, no. 1, 1989, pages 239 - 248, XP003000915
EL KHADEM H.S. ET AL.: "SYNTHESIS OF NITROGEN-BRIDGED PURINE-LIKE C-NUCLEOSIDES FROM ETHYL 2,5-ANHYDRO-6-O-BENZOYL-D-ALLONODITHIOATE", CARBOHYDRATE RESEARCH, vol. 189, 1989, pages 149 - 160, XP003000916
DAVEY D. ET AL.: "Cardiotonic Agents. 1. Novel 8-Aryl-Substituted Imidazo[1,2-a]- and -[1,5-a]pyridines and Imidazo[1,5-a]pyridinones as Potential Positive Inotropic Agents", J. MED. CHEM., vol. 30, 1987, pages 1337 - 1342, XP002339564
ABUSHANAB E. ET AL.: "Imidazo[1,5-a]pyrazines. IV. Aromatic Substitution Reactions", J. ORG. CHEM., vol. 40, no. 23, 1975, pages 3373 - 3375, XP003000918
ANDERSON S. ET AL.: "The n-Amination and Subsequent Oxidation by Bromide of Imidazo[1,5-a]-pyridines", J. CHEM. SOC. PERKIN TRANS, vol. 1, no. 16, 1976, pages 1722 - 1724, XP003000919
BLUHM M.E. ET AL.: "Complexes of Schiff Bases and Intermediates in the Copper-Catalyzed Oxidative Heterocyclization by Atmospheric Oxygen", INORGANIC CHEMISTRY, vol. 42, no. 26, 2003, pages 8878 - 8885, XP003000911
LIGTENBARG A.G. ET AL.: "Vanadium(v) complexes based on a bis(pyridine)-imine ligand (HL); synthesis and crystal structure of a dioxovanadium(v) complex involving a ligand cyclization", J. CHEM. SOC., DALTON TRANS., 1999, pages 659 - 661, XP001010414
ABUSHANAB E. ET AL.: "Imidazo[1,5-a]pyrazines. III. The Preparation and Chemistry of 3-(Phenylthiomethyl)imidazo[1,5-a]pyrazine (1,2)", J. HETEROCYCL. CHEM., vol. 12, no. 1, 1975, pages 207 - 209, XP003000913
GLOVER E.E. ET AL.: "Synthesis and Quaternization of Some Heterocyclic Mono- and Di-sulphides", J. CHEM. SOC., PERKIN TRANS, vol. 1, no. 21, 1973, pages 2595 - 2599, XP003000914
EL KHADEM H.S. ET AL.: "SYNTHESIS AND REARRANGEMENTS OF IMIDAZOLO- AND TRIAZOLO-DIAZINES", HETEROCYCLES, vol. 28, no. 1, 1989, pages 239 - 248, XP003000915
EL KHADEM H.S. ET AL.: "SYNTHESIS OF NITROGEN-BRIDGED PURINE-LIKE C-NUCLEOSIDES FROM ETHYL 2,5-ANHYDRO-6-O-BENZOYL-D-ALLONODITHIOATE", CARBOHYDRATE RESEARCH, vol. 189, 1989, pages 149 - 160, XP003000916
DAVEY D. ET AL.: "Cardiotonic Agents. 1. Novel 8-Aryl-Substituted Imidazo[1,2-a]- and -[1,5-a]pyridines and Imidazo[1,5-a]pyridinones as Potential Positive Inotropic Agents", J. MED. CHEM., vol. 30, 1987, pages 1337 - 1342, XP002339564
ABUSHANAB E. ET AL.: "Imidazo[1,5-a]pyrazines. IV. Aromatic Substitution Reactions", J. ORG. CHEM., vol. 40, no. 23, 1975, pages 3373 - 3375, XP003000918
ANDERSON S. ET AL.: "The n-Amination and Subsequent Oxidation by Bromide of Imidazo[1,5-a]-pyridines", J. CHEM. SOC. PERKIN TRANS, vol. 1, no. 16, 1976, pages 1722 - 1724, XP003000919
Attorney, Agent or Firm:
Konishi, Tomimasa (2-17-12 Marunouchi, Naka-k, Nagoya-shi Aichi 02, JP)
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