An intramolecular C-N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis
Status PubMed-not-MEDLINE Jazyk angličtina Země Německo Médium electronic-ecollection
Typ dokumentu časopisecké články
PubMed
26124890
PubMed Central
PMC4464440
DOI
10.3762/bjoc.11.99
Knihovny.cz E-zdroje
- Klíčová slova
- C–N cross-coupling, copper, enaminone, palladium, tetrahydroquinoline,
- Publikační typ
- časopisecké články MeSH
2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.
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