Title:
METHOD FOR PRODUCING PYRAZOLES, PYRAZOLE-TYPE DERIVATIVES AND APPLICATIONS THEREOF
Document Type and Number:
WIPO Patent Application WO/2014/122407
Kind Code:
A3
Abstract:
A method for preparing a pyrazole of formula (I), characterised in that it involves reacting a sydnone of formula (II) with an alkyne of formula (III) in the presence of copper, in order to obtain a pyrazole compound of formula that is then isolated and salified if desired.
Inventors:
TARAN FRÉDÉRIC (FR)
CHAUMONTET MANON (FR)
KOLODYCH SERGII (FR)
RASOLOFONJATOVO ANDOVOLA EVELIA (FR)
CHAUMONTET MANON (FR)
KOLODYCH SERGII (FR)
RASOLOFONJATOVO ANDOVOLA EVELIA (FR)
Application Number:
PCT/FR2014/050239
Publication Date:
November 27, 2014
Filing Date:
February 07, 2014
Export Citation:
Assignee:
COMMISSARIAT ENERGIE ATOMIQUE (FR)
International Classes:
C07D231/14; C07D231/12; C07D401/04; C07D401/12; C07D403/12; C07D407/12; C07D407/14; C07D409/04; C07H15/18
Foreign References:
| US3254093A | 1966-05-31 | |||
| US3063978A | 1962-11-13 |
Other References:
CHUNRUI WU ET AL: "Pd-catalyzed oxidative coupling of monosubstituted sydnones and terminal alkynes", TETRAHEDRON LETTERS, vol. 52, no. 29, July 2011 (2011-07-01), pages 3797 - 3801, XP055062602, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2011.05.058
DUNCAN L. BROWNE ET AL: "Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, no. 22, 10 June 2009 (2009-06-10), pages 7762 - 7769, XP055062606, ISSN: 0002-7863, DOI: 10.1021/ja902460n
KIRSI HARJU ET AL: "Solid-Phase Synthesis of Amino Acid Derived N -Unsubstituted Pyrazoles via Sydnones", ORGANIC LETTERS, vol. 11, no. 10, 21 May 2009 (2009-05-21), pages 2219 - 2221, XP055062641, ISSN: 1523-7060, DOI: 10.1021/ol900704b
DUNCAN L. BROWNE ET AL: "A Sydnone Cycloaddition Route to Pyrazole Boronic Esters", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 46, no. 45, 19 November 2007 (2007-11-19), pages 8656 - 8658, XP055062645, ISSN: 1433-7851, DOI: 10.1002/anie.200703767
SANTOS FUSTERO ET AL: "From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles", CHEMICAL REVIEWS, vol. 111, no. 11, 9 November 2011 (2011-11-09), pages 6984 - 7034, XP055062593, ISSN: 0009-2665, DOI: 10.1021/cr2000459
JONG YEON HWANG ET AL: "Solid-Phase Synthesis of 5-Amino-1-(Substituted Thiocarbamoyl)pyrazole and 1,2,4-Triazole Derivatives via Dithiocarbazate Linker", JOURNAL OF COMBINATORIAL CHEMISTRY, vol. 7, no. 1, January 2005 (2005-01-01), pages 136 - 141, XP055066306, ISSN: 1520-4766, DOI: 10.1021/cc049931n
JOSE A. CAMERANO ET AL: "Tris(pyrazolyl)borate carbosilane dendrimers and metallodendrimers", DALTON TRANSACTIONS, no. 44, January 2006 (2006-01-01), pages 5287, XP055137625, ISSN: 1477-9226, DOI: 10.1039/b608558j
VIKAS S PADALKAR ET AL: "Synthesis and characterization of novel 2, 2'-bipyrimidine fluorescent derivative for protein binding", CHEMISTRY CENTRAL JOURNAL, BIOMED CENTRAL LTD, LO, vol. 5, no. 1, 9 November 2011 (2011-11-09), pages 1 - 7, XP021094176, ISSN: 1752-153X, DOI: 10.1186/1752-153X-5-72
DUNCAN L. BROWNE ET AL: "Investigation of the Scope and Regiochemistry of Alkynylboronate Cycloadditions with Sydnones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, no. 22, 10 June 2009 (2009-06-10), pages 7762 - 7769, XP055062606, ISSN: 0002-7863, DOI: 10.1021/ja902460n
KIRSI HARJU ET AL: "Solid-Phase Synthesis of Amino Acid Derived N -Unsubstituted Pyrazoles via Sydnones", ORGANIC LETTERS, vol. 11, no. 10, 21 May 2009 (2009-05-21), pages 2219 - 2221, XP055062641, ISSN: 1523-7060, DOI: 10.1021/ol900704b
DUNCAN L. BROWNE ET AL: "A Sydnone Cycloaddition Route to Pyrazole Boronic Esters", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 46, no. 45, 19 November 2007 (2007-11-19), pages 8656 - 8658, XP055062645, ISSN: 1433-7851, DOI: 10.1002/anie.200703767
SANTOS FUSTERO ET AL: "From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles", CHEMICAL REVIEWS, vol. 111, no. 11, 9 November 2011 (2011-11-09), pages 6984 - 7034, XP055062593, ISSN: 0009-2665, DOI: 10.1021/cr2000459
JONG YEON HWANG ET AL: "Solid-Phase Synthesis of 5-Amino-1-(Substituted Thiocarbamoyl)pyrazole and 1,2,4-Triazole Derivatives via Dithiocarbazate Linker", JOURNAL OF COMBINATORIAL CHEMISTRY, vol. 7, no. 1, January 2005 (2005-01-01), pages 136 - 141, XP055066306, ISSN: 1520-4766, DOI: 10.1021/cc049931n
JOSE A. CAMERANO ET AL: "Tris(pyrazolyl)borate carbosilane dendrimers and metallodendrimers", DALTON TRANSACTIONS, no. 44, January 2006 (2006-01-01), pages 5287, XP055137625, ISSN: 1477-9226, DOI: 10.1039/b608558j
VIKAS S PADALKAR ET AL: "Synthesis and characterization of novel 2, 2'-bipyrimidine fluorescent derivative for protein binding", CHEMISTRY CENTRAL JOURNAL, BIOMED CENTRAL LTD, LO, vol. 5, no. 1, 9 November 2011 (2011-11-09), pages 1 - 7, XP021094176, ISSN: 1752-153X, DOI: 10.1186/1752-153X-5-72
Attorney, Agent or Firm:
PERIN, Georges et al. (52 rue de la Victoire, Paris Cedex 09, FR)
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