Paracyclophanes: Extending the Bridges. Synthesis

Abstract

Preparatively satisfactory routes to [3.2]paracyclophane (10), [4.2]paracyclophane (14), [4.3]paracyclophane (19) as well as several derivatives of these compounds -among others the bromides 25, the ester 31, the diesters 40-43 -are described using well-established methods of cyclophane chemistry (ring-closure reactions leading to thiacyclophanes, ring con-

Photochemical electrocyclic ring closure and leaving group expulsion from N-(9-oxothioxanthenyl)benzothiophene carboxamides

“…To 1.2 g (5.0 mmol) of 2-methylaminothioxanthen-9-one (13) 10 and 15 mL of triethylamine in 20 mL of anhyd CH 2 Cl 2 was added 1.7 g (5.9 mmol) of 3-chloro-2-(chlorocarbonyl)benzo[b]thiophene-6-carboxylic acid methyl ester (12) 4 . To a solution of 1.0 g (2.1 mmol) of acid 9 (LG -= Cl -) in 10 mL DMF was added 0.75 mL (0.78 g, 6.3 mmol) of benzyl mercaptan followed by 1.…”

Dynamics of [n.3]paracyclophanes (n = 2 - 4) as studied by NMR. Obtaining separate Arrhenius parameters for two dynamic processes in [4.3]paracyclophane

“…[3.2]Paracyclophane 1 and [4.3]paracyclophane 3 were obtained and purified according to a published procedure . VT 1 H NMR measurements were performed for the solutions of 1 in CD 2 Cl 2 and of 3 in a Freon R12/CD 2 Cl 2 mixture (10:1 v/v), degassed, and sealed in NMR tubes of the outer diameter of 5 mm.…”

Targeting the Heat Shock Protein 90 Dimer with Dimeric Inhibitors

“…The boronic acid was coupled with methyl 3-iodo-4-(2-methoxy-2-oxoethyl)benzoate ( 86 ) 39 under standard Suzuki coupling conditions38 to yield triester 87 . The aliphatic ester was selectively reduced to alcohol 88 , followed by cleavage of the methyl ether to give the free phenol.…”