Synthesis of organoselenyl isoquinolinium imides via iron(III) chloride-mediated tandem cyclization/selenation of N '-(2-alkynylbenzylidene)hydrazides and diselenides

This report describes the synthesis of organoselenyl isoquinolinium imides through a tandem cyclization between N'-(2-alkynylbenzylidene)hydrazides and diselenides. The reaction was carried out at room temperature under an ambient atmosphere using cheap iron(iii) chloride as the metallic source...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-10, Vol.18 (38), p.7577-7584
Main Authors: Yao, Hai-Feng, Wang, Dian-Liang, Li, Fang-Hui, Wu, Bing, Cai, Zhong-Jian, Ji, Shun-Jun
Format: Article
Language:English
Subjects:
Crystallography
Cycloaddition
Ferric chloride
Hydrazides
Imides
Iron
Iron chlorides
Room temperature
Selenides
Silver
Synthesis
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Summary:This report describes the synthesis of organoselenyl isoquinolinium imides through a tandem cyclization between N'-(2-alkynylbenzylidene)hydrazides and diselenides. The reaction was carried out at room temperature under an ambient atmosphere using cheap iron(iii) chloride as the metallic source. The strategy shows good tolerance to a broad range of N'-(2-alkynylbenzylidene)hydrazides and diselenides, and forms C-N and C-Se bonds in one step. The obtained product is further transformed into a bioactive H-pyrazolo[5,1-a]isoquinoline skeleton easily via a silver catalyzed [3 + 2] cycloaddition.
ISSN:1477-0520
1477-0539
DOI:10.1039/D0OB01517B