Development of new approach for the synthesis of 6-perfluoroalkyl substituted allene benzazecines and study of the nature of properties due to the presence of perfluoroalkyl groups

New approach for the introduction of a perfluoroalkynyl fragment into 1-R2–2-methyl-1,2,3,4-tetrahydroisoquinolines has been developed. Synthesized 1,1-disubstituted isoquinoline compounds under the action of methyl propiolate (24 °C) and acetylacetylene (-17 °C) in trifluoroethanol are converted into 6-perfluoroalkyl substituted allene benzazecines. The synthesized isoquinoline derivatives 2, and benzazecines 3–4 were evaluated against four cancer cell lines. The results revealed that compound 2h (R2 = C6H4-p-OMe; RF = CF(CF3)2) displayed good cytotoxic effects on four tested cell lines with IC50 values ranging from 5 to 50 μM. © 2023 Elsevier B.V.