David R. R. Moreno 1, Giorgio Giorgi 2, Cristian O. Salas 1 and Ricardo A. Tapia 1,*
1 Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de
Chile, Santiago 7820436, Chile; E-Mails: email@example.com (D.R.R.M.); firstname.lastname@example.org (C.O.S.)
2 Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia,
Universidad Complutense, Madrid 28040, Spain;E-Mail: email@example.com
* Author to whom correspondence should be addressed; E-Mail: firstname.lastname@example.org;
Tel.: +56-2-2354-4429; Fax: +56-2-2354-4744.
In conclusion, we have developed a short synthesis of dibenzo[b,f]oxepin derivatives using SNAr
and intramolecular McMurry reactions. An efficient process to obtain diarylethers through SNAr
reaction of salicylaldehydes with fluorobenzaldehydes using microwave irradiation is described.
McMurry reaction of diarylethers using TiCl4 and Zn in THF afforded the target tricyclic system in
reasonable yields (53%–55%). Further work on the synthesis of natural and pharmacologically active
dibenzo[b,f]oxepins are under way.
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ONE EXAMPLE SEE BELOW
Stilbene 3 (215 mg, 0.5 mmol) was added to a solution of KOH (900 mg,
16 mmol) in a mixture of EtOH (15 mL) and H2O (15 mL) and the suspension was heated under reflux
for 1 h. After cooling, the reaction mixture was acidified with aqueous HCl (10%) to pH 4 and
extracted with CH2Cl2 (3 × 25 mL). The combined organic extracts were washed with saturated
aqueous NaHCO3, dried, and filtered through a short column of silica gel. After the removal of the
solvent, the residue was dissolved in DMSO (5.0 mL) and Cs2CO3 (651.6 mg, 2.0 mmol) was added.
The reaction mixture was heated in a microwave reactor at 180 °C for 15 min. After cooling, the
solvent was evaporated under reduced pressure and the crude product was purified by flash column
chromatography (silica gel, EtOAc-hexanes; 1:9) to afford 5a (70 mg, 72%),
mp 108.5–109.5 °C
(Lit. 106–108 °C , 110–111 °C ).
IR (KBr): max 3069, 3044, 1483, 798 cm−1.
1H-NMR (acetone-d6) δ 6.82 (s, 2H, Two protons of -CH=CH- ), 7,19 (t, J = 7,8 Hz, 2H), 7.25 (d, J = 7.8 Hz, 2H), 7.30 (d, J = 7.8 Hz,2H), 7.38 (t, J = 7.8 Hz, 2H).
13C-NMR (acetone-d6) δ 122.9, 126.6, 131.1, 131.6, 131.7, 132.3, 159.1.
The Mapuche people were the original inhabitants of southern and central Chile.
Parinacota volcano in northern Chile
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