Competing Domino Knoevenagel-Cyclization Sequences with N-Arylcinnamylamines.
J Org Chem
; 89(10): 6937-6950, 2024 May 17.
Article
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| MEDLINE
| ID: mdl-38691817
ABSTRACT
Domino Knoevenagel-cyclization reactions of N-arylcinnamylamines were carried out with active methylene reagents, which took place with five competing cyclization mechanisms intramolecular hetero Diels-Alder reaction, stepwise polar [2 + 2] cycloaddition, styryl or aza-Diels-Alder reactions followed by rearomatization, and [1,5]-hydride shift-6-endo cyclization. In the stepwise aza-Diels-Alder reaction, the N-vinylpyridinium moiety acted as an azadiene, producing a condensed heterocycle with tetrahydroquinolizinium and tetrahydroquiniline subunits. Antiproliferative activity with low micromolar IC50 values was identified for some of the novel scaffolds.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2024
Tipo del documento:
Article
País de afiliación:
Hungria
Pais de publicación:
Estados Unidos