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Convenient Route to Quinoline-Tetrahydroquinolines from Quinoline-Carboxaldehydes

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Abstract:

Quinoline and tetrahydroquinoline structures are essential feature of many natural products. These heterocycles play a key role in heterocyclic and medicinal chemistry. Their synthesis by various methodologies has been published extensively1–3. However, in comparison to these systems, general synthetic methods of the preparation of diversely linked bisquinolines have been less developed. On the other hand, several N,N-(bisquinolin-4yl)(hetero)alkanediamines may be useful agents against chloroquineresistant malaria4–6. As a part of our research program on the chemistry of homoallylamines containing a (hetero)aromatic ring towards the synthesis of bioactive N-heterocycles7,8, we are pursuing investigations on the synthesis of 1,2,3,4-tetrahydroquinolines containing quinoline nucleus. In the present paper, we report a simply and efficient two step synthesis of 2-(8'quinolinyl)- and 2-(2'-quinolinyl)-1,2,3,4-tetrahydroquinolines using 6-exotrig process where allyl group of accessible 4-N-arylamino-4-quinolinyl-1butenes acts as an internal electrophilic C3 synthon8,9. The proposed route is based on our experience in the construction of diverse heterocycles containing nitrogen via cationic intramolecular cyclisation reactions of similar N-phenyl substituted amino-l -butenes (homoallylamines) that are very versatile starting materials, possessing an π-electron rich aromatic ring and an ally! fragment10–12.

Tópico:

Synthesis and bioactivity of alkaloids

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SCImago Journal & Country Rank
FuenteBiodiversity
Cuartil año de publicaciónNo disponible
VolumenNo disponible
IssueNo disponible
Páginas383 - 386
pISSNNo disponible
ISSN2160-0651

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