期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 26, 页码 5789-5797出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500704
关键词
Synthetic methods; Domino reactions; Cyclization; Nitrogen heterocycles; Ketenimine
资金
- National Natural Science Foundation of China (NSFC) [21272204, J1210042]
From readily available propargylic amines, 1,2,5-trisubstituted imidazoles are efficiently obtained through a cascade reaction catalyzed by AgOTf or promoted by molecular iodine. The AgOTf-catalyzed reaction involves nucleophilic addition of propargylic amine to ketenimine, a silver-catalyzed electrophilic cyclization reaction of alkyne, and a tautomerism/isomerism/metal-H exchange cascade. The iodine-mediated counterpart yields 5-formyl-1,2-disubtituted imidazoles, which presumably includes a cascade hydrolysis/oxidation reaction. Furthermore, the presented protocol can be scaled up and the resultant 1,2,5-trisubstituted imidazole can be converted into fused indeno[1,2-d]imidazole.
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