An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis
| Autor: | Petr Šimůnek, Hana Doušová, Radim Horak, Zdeňka Růžičková |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
C–N cross-coupling
biology Chemistry Organic Chemistry chemistry.chemical_element Angustureine Galipea biology.organism_classification palladium Combinatorial chemistry Full Research Paper enaminone Galipinine lcsh:QD241-441 tetrahydroquinoline lcsh:Organic chemistry Intramolecular force copper Officinalis Moiety lcsh:Q lcsh:Science Amination Palladium |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 11, Iss 1, Pp 884-892 (2015) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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