METHOD OF MANUFACTURING TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, METHOD OF MANUFACTURING TRIFLUOROMETHYL COMPOUND STARTING FROM TRIFLUOROMETHYL SUBSTITUTED SEMISQUARATE, AND TRIFLUOROMETHYL GROUP-CONTAINING COMPOUND

Title:

Document Type and Number:

WIPO Patent Application WO/2016/199789

Kind Code:

A1

Abstract:

The present invention addresses the problem of efficiently synthesizing a trifluoromethyl substituted semisquarate in a short process, in order to manufacture trifluoromethyl compounds with various functionalities. A method was developed of synthesizing a trifluoromethyl substituted semisquarate with squarate as a starting material, in the two steps of a trifluoromethylation reaction and an allyl alcohol transfer reaction. Furthermore, a method was established of manufacturing trifluoromethyl compounds with various functionalities starting from a trifluoromethyl substituted semisquarate.

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Inventors:

YAMAMOTO YOSHIHIKO (JP)
KUROHARA TAKASHI (JP)
SHIBUYA MASATOSHI (JP)

Application Number:

PCT/JP2016/066988

Publication Date:

December 15, 2016

Filing Date:

June 08, 2016

Export Citation:

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Assignee:

NAT UNIV CORP NAGOYA UNIV (JP)

International Classes:

C07C45/51; C07C45/68; C07C46/00; C07C49/753; C07C50/28; C07C50/32; C07C50/34; C07D209/88; C07D307/86; C07D307/91; C07D333/54; C07D333/76; C07D405/04; C07D455/02; C07D471/04; C07D513/04; C07B61/00

Foreign References:

JPH09502157A	1997-03-04
JPH07502007A	1995-03-02

Other References:

EMMA PACKARD ET AL.: "Organoytterbium Ate Complexes Extend the Value of Cyclobutenediones as Isoprene Equivalents", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 52, no. 49, 2013, pages 13076 - 13079, XP055333588
YOSHIHIKO YAMAMOTO ET AL.: "Radical-Mediated Ring Enlargement of Cyclobutenones: New Synthetic Potential of Squaric Acid", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 117, no. 38, 1995, pages 9653 - 9661, XP055333590
LANNY S. LIEBESKIND ET AL.: "An Inproved Method for the Synthesis of Substituted Cyclobutenediones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 53, no. 11, 1988, pages 2482 - 2488, XP055333591
TERUAKI MUKAIYAMA ET AL.: "Lithium Acetate- catalyzed Trifluoromethylation of Carbonyl Compounds with (Trifluoromethyl)trimethylsilane", CHEMISTRY LETTERS, vol. 34, no. 1, 2005, pages 88 - 89, XP055333596