Title:
METHOD FOR PRODUCING PYRAZOLE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2016/152886
Kind Code:
A1
Abstract:
The present invention provides a novel method for producing pyrazole derivatives useful as intermediates of pharmaceuticals and agricultural chemicals, as well as novel intermediate compounds in this method. The present invention pertains to a method for producing a pyrazole derivative (6) by reacting a compound (5) and an oxidizer. (In the formula, R1, R2, R3, X1, X2, and Z1 are as defined in the claims and specification.)
Inventors:
ISHIBASHI YUICHIRO (JP)
OCHI YOUSUKE (JP)
MIYAKE NORIAKI (JP)
YAMAZAKI YUSUKE (JP)
SHIMIZU SHOTA (JP)
OCHI YOUSUKE (JP)
MIYAKE NORIAKI (JP)
YAMAZAKI YUSUKE (JP)
SHIMIZU SHOTA (JP)
Application Number:
PCT/JP2016/059101
Publication Date:
September 29, 2016
Filing Date:
March 23, 2016
Export Citation:
Assignee:
ASAHI GLASS CO LTD (JP)
International Classes:
C07D231/14; C07C221/00; C07C225/14; C07D231/12
Domestic Patent References:
WO2014160668A1 | 2014-10-02 | |||
WO2012176717A1 | 2012-12-27 | |||
WO2015003289A1 | 2015-01-15 | |||
WO2012009009A2 | 2012-01-19 | |||
WO1995004725A1 | 1995-02-16 | |||
WO2015105129A1 | 2015-07-16 |
Foreign References:
JP2010531314A | 2010-09-24 | |||
JP2010534626A | 2010-11-11 | |||
JP2011518767A | 2011-06-30 | |||
JP2010501502A | 2010-01-21 | |||
JP2013006781A | 2013-01-10 | |||
JP2013006778A | 2013-01-10 | |||
JP2010116334A | 2010-05-27 | |||
JP2010540477A | 2010-12-24 | |||
JP2007509850A | 2007-04-19 | |||
JP2005511782A | 2005-04-28 | |||
JP2010531315A | 2010-09-24 | |||
JP2010513411A | 2010-04-30 | |||
JP2001125224A | 2001-05-11 | |||
JPH08198857A | 1996-08-06 | |||
CN105541716A | 2016-05-04 | |||
CN104945325A | 2015-09-30 | |||
CN104496903A | 2015-04-08 |
Other References:
GHOSH C. K. ET AL.: "Heterocyclic System II. Electrophilic Substitution on 1-Phenyl-4-(2- hydroxybenzoyl)pyrazole", JOURNAL OF THE INDIAN CHEMICAL SOCIETY, vol. 55, no. 3, 1978, pages 268 - 271, XP009506192, ISSN: 0019-4522
ZIKAN V ET AL.: "Substanzen mit Antineoplastischer Wirkung XIX. Substituterte Pyrazole Durch Reaktion Von beta-4- Methoxybenzoyl-beta-chlor(brom)acrylsaure mit Diazomethan", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 32, no. 10, 1967, pages 3587 - 3596, XP055485144, ISSN: 1212-6950
OKADA ETSUJI ET AL.: "Facile Synthetic Methods for 3- and 5-Trifluoromethyl-4-Trifluoroacetyl- Pyrazoles and Their -Conversion into Pyrazole- 4-Carboxylic Acids", HETEROCYCLES, vol. 34, no. 4, 1992, pages 791 - 798, XP009103121, ISSN: 1881-0942
TANAKA KIYOSHI ET AL.: "Reactions of Trifluoroacetonitrile Oxide or -nitrilimines with beta-Diketones and beta- Keto Esters", BULLETIN OF CHEMICAL SOCIETY OF JAPAN, vol. 59, 1986, pages 2631 - 2632, XP002688704, ISSN: 0009-2673
VASIL'EV L.S. ET AL.: "2-(N-Alkylamino)-1- (trifluoroacetimidoyl)vinyl ketone derivatives as potential reagents in heterocyclic synthesis", RUSSIAN CHEMICAL BULLETIN, vol. 57, no. 11, 2008, pages 2359 - 2363, XP019753329, ISSN: 1066-5285
HAMMOUDA H. A. ET AL.: "1- Benzoyl-1- Phenylhydrazine as a Pyrazole Precursor", ACTA CHIMICA HUNGARICA, vol. 116, no. 1, 1984, pages 21 - 27, XP009506179, ISSN: 0231-3146
TOUZOT ALINE ET AL.: "Synthesis of trifluoromethylated pyrazoles from trifluoromethylenaminones and monosubstituted hydrazines", JOURNAL OF FLUORINE CHEMISTRY, vol. 125, 2004, pages 1299 - 1304, XP004534450, ISSN: 0022-1139
SINIGH SHIV. P. ET AL.: "A Facile Synthesis of 5- Methyl-1-(phenyl/heterocyclyl)-4- trifluoroacethylpyrazoles", JOURNAL OF CHEMICAL RESEARCH SYNOPSES, 1997, pages 142 - 143, XP055315912, ISSN: 0308-2342
SCHMITT ETIENNE ET AL.: "In Situ Generated Fluorinated Iminium Salts for Difluoromethylation and Difluoroacetylation", ORGANIC LETTERS, vol. 17, no. 18, pages 4510 - 4513, XP055485150, ISSN: 1523-7052
See also references of EP 3275868A4
ZIKAN V ET AL.: "Substanzen mit Antineoplastischer Wirkung XIX. Substituterte Pyrazole Durch Reaktion Von beta-4- Methoxybenzoyl-beta-chlor(brom)acrylsaure mit Diazomethan", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 32, no. 10, 1967, pages 3587 - 3596, XP055485144, ISSN: 1212-6950
OKADA ETSUJI ET AL.: "Facile Synthetic Methods for 3- and 5-Trifluoromethyl-4-Trifluoroacetyl- Pyrazoles and Their -Conversion into Pyrazole- 4-Carboxylic Acids", HETEROCYCLES, vol. 34, no. 4, 1992, pages 791 - 798, XP009103121, ISSN: 1881-0942
TANAKA KIYOSHI ET AL.: "Reactions of Trifluoroacetonitrile Oxide or -nitrilimines with beta-Diketones and beta- Keto Esters", BULLETIN OF CHEMICAL SOCIETY OF JAPAN, vol. 59, 1986, pages 2631 - 2632, XP002688704, ISSN: 0009-2673
VASIL'EV L.S. ET AL.: "2-(N-Alkylamino)-1- (trifluoroacetimidoyl)vinyl ketone derivatives as potential reagents in heterocyclic synthesis", RUSSIAN CHEMICAL BULLETIN, vol. 57, no. 11, 2008, pages 2359 - 2363, XP019753329, ISSN: 1066-5285
HAMMOUDA H. A. ET AL.: "1- Benzoyl-1- Phenylhydrazine as a Pyrazole Precursor", ACTA CHIMICA HUNGARICA, vol. 116, no. 1, 1984, pages 21 - 27, XP009506179, ISSN: 0231-3146
TOUZOT ALINE ET AL.: "Synthesis of trifluoromethylated pyrazoles from trifluoromethylenaminones and monosubstituted hydrazines", JOURNAL OF FLUORINE CHEMISTRY, vol. 125, 2004, pages 1299 - 1304, XP004534450, ISSN: 0022-1139
SINIGH SHIV. P. ET AL.: "A Facile Synthesis of 5- Methyl-1-(phenyl/heterocyclyl)-4- trifluoroacethylpyrazoles", JOURNAL OF CHEMICAL RESEARCH SYNOPSES, 1997, pages 142 - 143, XP055315912, ISSN: 0308-2342
SCHMITT ETIENNE ET AL.: "In Situ Generated Fluorinated Iminium Salts for Difluoromethylation and Difluoroacetylation", ORGANIC LETTERS, vol. 17, no. 18, pages 4510 - 4513, XP055485150, ISSN: 1523-7052
See also references of EP 3275868A4
Attorney, Agent or Firm:
TAKASHIMA, HAJIME (JP)
Takashima 1 (JP)
Takashima 1 (JP)
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