Title:
NOVEL PREPARATION METHOD FOR 4-THIOCYANO-1,4,5-TRISUBSTITUTED 1,2,3-TRIAZOLE
Document Type and Number:
WIPO Patent Application WO/2021/088296
Kind Code:
A1
Abstract:
A preparation method for 4-thiocyano-1,4,5-trisubstituted 1,2,3-triazole, comprising the following step: in an organic solvent, under the action of a copper hexafluorophosphate tetraacetonitrile catalyst, catalyzing a thiocyanato internal alkyne compound to react with an organic azide compound to prepare 4-thiocyanato-1,4,5-trisubstituted 1,2,3-triazole.
Inventors:
ZHENG NAN (CN)
SONG WANGZE (CN)
LI MING (CN)
ZHENG YUBIN (CN)
SONG WANGZE (CN)
LI MING (CN)
ZHENG YUBIN (CN)
Application Number:
PCT/CN2020/080157
Publication Date:
May 14, 2021
Filing Date:
March 19, 2020
Export Citation:
Assignee:
UNIV DALIAN TECH (CN)
International Classes:
C07D249/06; C07D249/04
Domestic Patent References:
| WO2009083457A1 | 2009-07-09 |
Foreign References:
| CN110746365A | 2020-02-04 | |||
| CN109320469A | 2019-02-12 | |||
| CN109096214A | 2018-12-28 | |||
| JP2019059689A | 2019-04-18 |
Other References:
LI MING, DONG KUN, ZHENG YUBIN, SONG WANGZE: "Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 46, 27 November 2019 (2019-11-27), pages 9933 - 9941, XP055810449, ISSN: 1477-0520, DOI: 10.1039/C9OB02081K
BHATT DIVYA, SINGH PRASOON RAJ, KALARAMNA PRATIBHA, KUMAR KRISHN, GOSWAMI AVIJIT: "An Atom‐Economical Approach to 2‐Triazolyl Thio‐/Seleno Pyridines via Ruthenium‐Catalyzed One‐pot [3+2]/[2+2+2] Cycloadditions", ADVANCED SYNTHESIS AND CATALYSIS, vol. 361, no. 23, 3 December 2019 (2019-12-03), pages 5483 - 5489, XP055810451, ISSN: 1615-4150, DOI: 10.1002/adsc.201900791
DAVID V. PARTYKA, LEI GAO, THOMAS S. TEETS, JAMES B. UPDEGRAFF, NIHAL DELIGONUL, THOMAS G. GRAY: "Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide. Syntheses, Structures, and Optical Properties", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 28, no. 21, 9 November 2009 (2009-11-09), pages 6171 - 6182, XP055520316, ISSN: 0276-7333, DOI: 10.1021/om9005774
SONG WANGZE, LI MING, DONG KUN, ZHENG YUBIN: "Ruthenium‐Catalyzed Highly Regioselective Azide‐Internal Thiocyanatoalkyne Cycloaddition under Mild Conditions: Experimental and Theoretical Studies", ADVANCED SYNTHESIS AND CATALYSIS, vol. 361, no. 22, 19 November 2019 (2019-11-19), pages 5258 - 5263, XP055810454, ISSN: 1615-4150, DOI: 10.1002/adsc.201901014
HUANG PING; SU QIONG; DONG WANRONG; ZHANG YINGJUN; AN DELIE: "BrØnsted/Lewis acids-promoted selective preparations of 3-hetero quinolines or 4/5-hetero triazoles from azides and hetero-alkynes", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 73, no. 30, 25 May 2017 (2017-05-25), AMSTERDAM, NL, pages 4275 - 4284, XP085110380, ISSN: 0040-4020, DOI: 10.1016/j.tet.2017.05.076
BHATT DIVYA, SINGH PRASOON RAJ, KALARAMNA PRATIBHA, KUMAR KRISHN, GOSWAMI AVIJIT: "An Atom‐Economical Approach to 2‐Triazolyl Thio‐/Seleno Pyridines via Ruthenium‐Catalyzed One‐pot [3+2]/[2+2+2] Cycloadditions", ADVANCED SYNTHESIS AND CATALYSIS, vol. 361, no. 23, 3 December 2019 (2019-12-03), pages 5483 - 5489, XP055810451, ISSN: 1615-4150, DOI: 10.1002/adsc.201900791
DAVID V. PARTYKA, LEI GAO, THOMAS S. TEETS, JAMES B. UPDEGRAFF, NIHAL DELIGONUL, THOMAS G. GRAY: "Copper-Catalyzed Huisgen [3 + 2] Cycloaddition of Gold(I) Alkynyls with Benzyl Azide. Syntheses, Structures, and Optical Properties", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 28, no. 21, 9 November 2009 (2009-11-09), pages 6171 - 6182, XP055520316, ISSN: 0276-7333, DOI: 10.1021/om9005774
SONG WANGZE, LI MING, DONG KUN, ZHENG YUBIN: "Ruthenium‐Catalyzed Highly Regioselective Azide‐Internal Thiocyanatoalkyne Cycloaddition under Mild Conditions: Experimental and Theoretical Studies", ADVANCED SYNTHESIS AND CATALYSIS, vol. 361, no. 22, 19 November 2019 (2019-11-19), pages 5258 - 5263, XP055810454, ISSN: 1615-4150, DOI: 10.1002/adsc.201901014
HUANG PING; SU QIONG; DONG WANRONG; ZHANG YINGJUN; AN DELIE: "BrØnsted/Lewis acids-promoted selective preparations of 3-hetero quinolines or 4/5-hetero triazoles from azides and hetero-alkynes", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 73, no. 30, 25 May 2017 (2017-05-25), AMSTERDAM, NL, pages 4275 - 4284, XP085110380, ISSN: 0040-4020, DOI: 10.1016/j.tet.2017.05.076
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