ChemInform Abstract: Copper-Catalyzed 1,2-Double Amination of 1-Halo-1-alkynes. Concise Synthesis of Protected Tetrahydropyrazines and Related Heterocyclic Compounds

Autor:	Hiroyuki Naito, Hirokazu Urabe, Takeshi Hata, Yasuhiro Fukudome
Rok vydání:	2008
Předmět:	chemistry.chemical_compound chemistry Diamine Copper catalyzed Moiety General Medicine Ring (chemistry) Medicinal chemistry Derivative (chemistry) Amination Catalysis
Zdroj:	ChemInform. 39
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200825163
Popis:	Reaction of N,N‘-di(p-toluenesulfonyl)-1,2-diamine, 1-bromo-1-alkyne, K3PO4, and a catalytic amount of CuI in hot DMF afforded N,N‘-di(p-toluenesulfonyl)-1,2,3,4-tetrahydropyrazines in good yields. The reaction most likely involves (i) monoalkynylation of the diamine derivative with 1-bromo-1-alkyne, and (ii) 6-endo-dig ring closure between the acetylenic bond and another sulfonylamine moiety of the diamine. When the starting 1,2-diamine derivative was replaced with N,N‘-di(p-toluenesulfonyl)-1,3-diamine or N-(p-toluenesulfonyl)-2-amino-1-ethanol, the corresponding seven-membered diazacycle or six-membered N,O-heterocycle was produced. In addition, 1,1-dibromo-1-alkene could be used in place of 1-bromo-1-alkyne.
Databáze:	OpenAIRE
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