An efficient route to 1-formyl-1,2-dihydroquinolines 6 is described based on the BF3-catalyzed cyclization of o-(1-hydroxy-2-alkenyl)phenyl isocyanides 4, which can be prepared feasibly by the reaction of N-(o-acylphenyl)formamides 1 with alkenylmagnesium bromides 2 followed by treatment of the resulting hydroxy formamides 3 with phosphorous oxychloride.
A new dendrimer (1), which contains phenol groups in the exterior for solubilization in
aqueous alkaline solution and calix[4]resorcinarene in the interior to increase the molecular
weight and number of the phenol group even in the lower generation, was designed as new
negative-working, alkaline-developable photoresist material. A negative-working photoresist
based on 1, 2,6-bis(hydroxymethyl)phenol as cross-linker, and diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate as a photoacid generator has been developed. This resist
gave a clear negative pattern through postbaking at 110 °C after exposure to UV light,
followed by developing with a 0.3% aqueous tetramethylammonium hydroxide solution at
room temperature.
Chiral calix[4]resorcinarenes were prepared via mono-O-benzylation, and their conformational properties in solution were described. The complexation behavior of the heptahydroxy derivative with a chiral trimethylammonium compound in methanol was investigated by 1H NMR spectroscopy.
The cyclocondensation of 2-alkylresorcinols with 1,3,5-trioxane in ethanol-conc. HCI (4: 1 v/v) produced calix[4lresorcinarerie and calix[6]resorcinarene; the latter was isomerized to the former on prolonged heating in the reaction media.
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