Title:
METHOD FOR PRODUCING α-AZIDOANILINE DERIVATIVE OR α, α'-DIAZIDE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2020/004043
Kind Code:
A1
Abstract:
The present invention provides a method which uses an aniline derivative as a starting material, and which is capable of producing an α-azidoaniline derivative or an α, α'-diazide derivative. The present invention comprises a method for producing an α-azidoaniline derivative represented by formula (2) or an α, α'-diazide derivative by bringing an aniline derivative represented by formula (1) and an azidizing agent into contact with each other in the presence of water, a persulfuric acid salt and a copper compound. (In formula (1), each one of R1 to R5 independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1-12 carbon atoms, a substituted or unsubstituted alkoxy group having 1-12 carbon atoms, a substituted or unsubstituted aralkyl group having 7-14 carbon atoms, a substituted or unsubstituted aryl group having 2-13 carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2-7 carbon atoms, or a substituted or unsubstituted carbonyl group having 1-20 carbon atoms; or alternatively, adjacent moieties among R1 to R5 may combine together to form an aliphatic hydrocarbon ring, an aromatic ring or a heterocyclic ring. In formula (2), R1 to R3 and R5 are the same as R1 to R3 and R5 in formula (1); and R4 represents an azide group (N3), or is the same as R4 in formula (1).)
Inventors:
SEKI MASAHIKO (JP)
Application Number:
PCT/JP2019/023333
Publication Date:
January 02, 2020
Filing Date:
June 12, 2019
Export Citation:
Assignee:
TOKUYAMA CORP (JP)
International Classes:
C07C247/16; B01J27/055; B01J31/04; C07C227/18; C07C229/60; C07C247/18; C07D235/26; C07B61/00
Domestic Patent References:
| WO2006015134A1 | 2006-02-09 | |||
| WO2015173970A1 | 2015-11-19 | |||
| WO2012018325A1 | 2012-02-09 |
Foreign References:
| CN106478594A | 2017-03-08 | |||
| JP2016028016A | 2016-02-25 |
Other References:
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GOSWAMI, M. ET AL.: "Porphyrin Co(III)-Nitrene Radical Mediated Pathway for Synthesis of o-Aminoazobenzenes", MOLECULES, vol. 23, no. 5, 1 May 2018 (2018-05-01), pages 1 - 11, XP055667247, DOI: 10.3390/molecules23051052
FANG, H. ET AL.: "Regioselective and Direct Azidation of Anilines via Cu(II)-Catalyzed C–H Functionalization in Water", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 20, 17 September 2017 (2017-09-17), pages 11212 - 11217, XP055667227, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b01594
DOU, Y. ET AL.: "Copper(II)-Catalyzed Direct Azidation of N -Acylated 8-Aminoquinolines by Remote C−H Activation", CHEMCATCHEM, vol. 8, no. 23, 21 September 2016 (2016-09-21), pages 3570 - 3574, XP055667229, ISSN: 1867-3880, DOI: 10.1002/cctc.201600874
HONGLI FANG, JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 20, 2017, pages 11212 - 11217
GOSWAMI, M. ET AL.: "Porphyrin Co(III)-Nitrene Radical Mediated Pathway for Synthesis of o-Aminoazobenzenes", MOLECULES, vol. 23, no. 5, 1 May 2018 (2018-05-01), pages 1 - 11, XP055667247, DOI: 10.3390/molecules23051052
FANG, H. ET AL.: "Regioselective and Direct Azidation of Anilines via Cu(II)-Catalyzed C–H Functionalization in Water", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 20, 17 September 2017 (2017-09-17), pages 11212 - 11217, XP055667227, ISSN: 0022-3263, DOI: 10.1021/acs.joc.7b01594
DOU, Y. ET AL.: "Copper(II)-Catalyzed Direct Azidation of N -Acylated 8-Aminoquinolines by Remote C−H Activation", CHEMCATCHEM, vol. 8, no. 23, 21 September 2016 (2016-09-21), pages 3570 - 3574, XP055667229, ISSN: 1867-3880, DOI: 10.1002/cctc.201600874
HONGLI FANG, JOURNAL OF ORGANIC CHEMISTRY, vol. 82, no. 20, 2017, pages 11212 - 11217
Attorney, Agent or Firm:
SSINPAT PATENT FIRM (JP)
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