123971-76-6Relevant academic research and scientific papers
Hydrogen Bonded Phenol-Quinolines with Highly Controlled Proton-Transfer Coordinate
Parada, Giovanny A.,Glover, Starla D.,Orthaber, Andreas,Hammarstr?m, Leif,Ott, Sascha
, p. 3365 - 3372 (2016/07/23)
A series of polycyclic phenols with intramolecular hydrogen bonds (IMHB) to quinolines was synthesized by Friedl?nder annulation of cycloalkanone-functionalized anisoles with 2-aminobenzaldehyde. The prepared compounds represent the first series of IMHB phenols in which the substitution and conjugation patterns between the phenols and the hydrogen bond acceptors are kept constant, and in which comparable electronic interaction between the two subunits is thus ensured. The distance and relative orientation between the phenolic OH and the quinolone nitrogen atom is controlled by 1,3-cycloalkadienes of different ring sizes to which the phenol and quinoline subunits are formally annulated.1H δ(OH) chemical shift and X-ray crystal structure characterization support the conclusion that the size and conformational preference of the 1,3-cycloalkadiene rings control the H-bond geometry and strength. As a result, the oxygen to nitrogen distances differ by as much as 0.30 ? across the series.
Furan Derivatives. Part 10. Synthesis of Cycloheptabenzofuran
Horaguchi, Takaaki,Hasegawa, Eietsu,Shimizu, Takahachi,Tanemura, Kiyoshi,Suzuki, Tsuneo
, p. 365 - 369 (2007/10/02)
Cycloheptabenzofuran 2 was synthesized by heating (5-oxo-5H-benzocyclohepten-4-yloxy)acetic acid 16 with sodium acetate in acetic anhydride or by photocyclization of 16 in acetonitrile.Several reactions of cycloheptabenzofuran 2 were examined.Protonation of 2 with trifluoroacetic acid occurred at the 2-position to give a tropylium ion 17.Catalytic hydrogenation of 2 with palladium on charcoal proceeded smoothly to give tetrahydrocycloheptabenzofuran 18.The Diels-Alder reaction of 2 with tetracyanoethylene produced an adduct 19.Formylation of 2 with phosphorus oxychloride and dimethylformamide occurred easily at the 2-position to afford compound 20.Cycloheptabenzofuran 2 has both properties of heptafulvene and benzofuran.
