Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ

Autor:	Althea S.-K. Tsang, Matthew H. Todd
Rok vydání:	2009
Předmět:	Nitromethane Organic Chemistry Substituent chemistry.chemical_element Iminium Ring (chemistry) Biochemistry Medicinal chemistry Ion chemistry.chemical_compound chemistry Drug Discovery Organic chemistry Isoquinoline Carbon Vicinal
Zdroj:	Tetrahedron Letters. 50:1199-1202
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2008.12.101
Popis:	The oxidation of N-phenyltetrahydroisoquinolines occurs rapidly with DDQ. Under ambient conditions and in the presence of nitromethane, the corresponding β-nitroamine derivatives are isolated in good to excellent yields. Variation in the electronic nature of the isoquinoline and the N-phenyl substituent showed that a broad range of substituents are tolerated, with electronic communication between the isoquinoline aromatic ring and the C1 carbon being stronger than with the N-aryl ring. Reduction of the β-nitroamines to the corresponding novel chiral vicinal diamines are straightforward. Examination of the reaction by 1H NMR spectroscopy suggested that the reaction proceeds via an iminium ion, which then reacts with nitromethane upon work-up. This information was used to shorten the required reaction time.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8b195ce88449707ba808f5c9a911f20f https://doi.org/10.1016/j.tetlet.2008.12.101 Zobrazit plný text záznamu Full Text from ScienceDirect