O. Hassan Omar, F. Babudri, G. M. Farinola, F. Naso, A. Operamolla
FULL PAPER
(2 mg, 0.012 mmol, 5 mol-%), triphenylphosphane (6 mg,
0.023 mmol, 10 mol-%), 10 (317 mg, 0.5 mmol), 4,7-dibro-
mobenzo[c][1,2,5]thiadiazole (68 mg, 0.23 mmol), and freshly dis-
tilled triethylamine (10 mL). The mixture was stirred for a few min-
utes at room temperature and then heated at 80 °C until the reac-
tion was complete (TLC analysis). After 2 h the reaction mixture
was then cooled to room temperature, neutralized with an aqueous
solution of 5% HCl (50 mL), and extracted with dichloromethane
(3ϫ50 mL). The organic layers were collected, washed with a satu-
rated solution of NaCl, dried with anhydrous Na2SO4, and concen-
trated under reduced pressure. The crude material obtained was
purified by preparative chromatography on silica gel (dichloro-
methane/PE/diethyl ether, 58:40:2). An orange solid (165 mg, 51%
yield) was isolated. M.p. 136–137 °C (dichloromethane/methanol).
C82H100N2O8S5 (1402.01): calcd. C 70.25, H 7.19, N 2.00, S 11.44;
found C 69.93, H 7.25, N 1.89, S 12.44. 1H NMR (400 MHz,
CDCl3): δ = 7.79 (s, 2 H, benzothiadiazole ring CH), 7.36 (br. s, 4
H, dithiolated ring CH), 7.18 (br. s, 2 H, dithiolated ring CH), 7.14
(br. s, 2 H, dialkoxy substituted rings), 7.04 (br. s, 2 H, dialkoxy
substituted rings CH), 4.03–4.12 (m, 16 H, benzyl CH2 and
OCH2CH2-), 2.37 (s, 12 H, S-acetyl CH3), 1.82–1.97 (m, 8 H, alkyl
chain CH2), 1.50–1.65 (m, 8 H, alkyl chain CH2), 1.22–1.46 (m, 32
H, alkyl chain CH2), 0.81–0.92 (m, 12 H, -CH2CH3) ppm. 13C
NMR (100 MHz, CDCl3): δ = 194.5 (C=O), 154.2, 154.0, 153.5,
138.2, 132.2, 130.7, 129.2, 124.0, 117.2, 117.0, 116.8, 114.7, 113.2,
94.6 (CϵC), 94.3 (CϵC), 90.9 (CϵC), 86.4 (CϵC), 69.75, 69.70,
32.98, 31.90, 30.38, 29.53, 29.44, 29.40, 26.14, 22.74, 14.18 ppm.
Acknowledgments
This work was financially supported by Ministero dell’Istruzione,
dell’Università e della Ricerca (MIUR), “Progetto PRIN 2007
PBWN44” and by Università degli Studi Aldo Moro di Bari.
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˜
1508, 1416, 1220, 1130, 1033, 801, 629 cm–1.
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1
17.99. H NMR (400 MHz, CDCl3): δ = 7.39 (br. s, 4 H, external
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6.7 Hz, 6 H, CH3) ppm. 13C NMR (100 MHz, CDCl3): δ = 153.6,
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69.6, 31.9, 29.43, 29.37, 29.32, 28.57, 26.11, 22.69, 14.12 ppm. IR
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Supporting Information (see footnote on the first page of this arti-
cle): Synthetic procedures and characterization data for com-
pounds 1 and 5–10.
536
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Eur. J. Org. Chem. 2011, 529–537