American Chemical Society
jo4c00299_si_001.pdf (12.65 MB)

Competing Domino Knoevenagel-Cyclization Sequences with N‑Arylcinnamylamines

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journal contribution
posted on 2024-05-01, 20:03 authored by Mihály Kajtár, Sándor Balázs Király, Attila Bényei, Attila Kiss-Szikszai, Anita Kónya-Ábrahám, Ning Zhang, Lilla Borbála Horváth, Szilvia Bősze, Dehai Li, Andras Kotschy, Attila Paczal, Tibor Kurtán
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.