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Abstract:
A Cu-catalyzed interrupted click reaction for the synthesis of 3-perfluoroalkyl-substituted 1,2,4-triazinones is developed. The reaction between the terminal alkynes with azides and pentafluoropropionic or heptafluorobutyric anhydride proceeds smoothly to afford the corresponding pentafluoroethylated or heptafluoropropyled products in good yields. This protocol is applicable to various types of substrates including arylacetylenes and aliphatic azides having electron-rich and electron deficient groups. The broad substrate scope and functional group tolerance of the reaction makes this approach a practical method for the synthesis of valuable 3-perfluoroalkyl-substituted 1,2,4-triazinones. Some of the title compounds showed fungicidal activity against cucumber downy mildew (CDM). (C) 2019 Elsevier Ltd. All rights reserved.
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TETRAHEDRON
ISSN: 0040-4020
Year: 2019
Issue: 19
Volume: 75
Page: 2843-2847
2 . 2 3 3
JCR@2019
2 . 1 0 0
JCR@2023
ESI Discipline: CHEMISTRY;
ESI HC Threshold:184
JCR Journal Grade:2
CAS Journal Grade:3
Cited Count:
WoS CC Cited Count: 13
SCOPUS Cited Count: 15
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 1
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