E. K. Unver et al. / Tetrahedron Letters 52 (2011) 2725–2729
2729
2. 4,9-Bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-
Supplementary data
[1,2,5]thiadiazolo[3,4-g]quinoxaline (7, HTTQ)
Supplementary data associated with this article can be found, in
4,7-Bis(4-hexylthien-2-yl)benzo[c][1,2,5]thiadiazole-5,6-diamine
(5) (100 mg, 0.20 mmol) was dissolved in EtOH (5 ml). 2,20-Thenil
(44.56 mg, 0.20 mmol) and a catalytic amount of p-TsOH were
added to the reaction medium. The mixture was stirred at room
temperature for 6 h. The solvent was evaporated under vacuum
and the crude product was purified by column chromatography
over silica gel, eluting with 1:1 (CH2Cl2/hexane) to give 7 as a green
solid (106 mg, 78%). 1H-NMR (400 MHz CDCl3): d (ppm) 8.62 (d,
J = 1.1 Hz, 2H), 7.51 (dd, J1 = 5.0, J2 = 0.9 Hz, 2H), 7.44 (dd, J1 = 3.7,
J2 = 0.9 Hz, 2H), 7.19 (br s, 2H), 6.97 (dd, J1 = 5.0, J2 = 3.7 Hz, 2H),
2.68 (t, J = 7.7 Hz, 4H), 1.68 (m, 4H), 1.32 (m, 12H), 0.84 (t,
J = 6.8 Hz, 6H). 13C NMR (100 MHz, CDCl3): d (ppm) 150.4, 144.3,
141.5, 140.2, 133.9, 133.3, 132.7, 129.9, 129.2, 126.0, 125.0,
119.1, 30.3, 29.2, 29.21, 27.7, 21.2, 12.7. MS (m/z) 685.2 [M+1]+.
References and notes
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845, 706, 579 cmꢀ1
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yl)pyrazino[2,3-g]quinoxaline (8, HTPQ)
A
mixture of 4,7-bis(4-hexylthien-2-yl)-5,6-dinitrobenzo[c]-
[1,2,5]thiadiazole (4) (200 mg, 0.36 mmol) and Zn dust (489 mg,
7.48 mmol) in glacial AcOH (3 mL) was stirred at 60 °C for 1 h until
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under vacuum and the crude product was purified by column chro-
matography over silica gel, eluting with 1:1 (CH2Cl2/hexane) to
give 8 as a shiny-black solid (145 mg, 48%). 1H NMR (400 MHz
CDCl3): d (ppm) 8.16 (s, 2H), 7.48 (d, J = 3.7 Hz, 4H), 7,46 (d,
J = 5.0 Hz, 4H), 7.27 (s, 2H), 6.94 (dd, J1 = 5.0, J2 = 3.7 Hz, 4H), 2.75
(t, J = 7.7 Hz, 4H), 1.77 (m, 4H), 1.35 (m, 12H), 0.84 (t, J = 7.0 Hz,
6H). 13C NMR (100 MHz, CDCl3): d (ppm) 144.0, 141.3, 141.1,
135.2, 134.8, 132.7, 129.5, 129.2, 126.5, 125.9, 124.7, 30.8, 29.8,
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28.2, 21.6, 13.1. MS (m/z) 843 [M+1]+. IR:
m = 3088, 2925, 1520,
1426, 1310, 1233, 1173, 1060, 853, 701, 598 cmꢀ1
.
Acknowledgments
The authors are grateful for a TUBA grant. Two of us (E.K.U and
S.T) acknowledge TUBITAK-Department of Science Fellowships and
grant Program.
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