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17. Krishnakumar, B.; Velmurugan, R.; Jothivel, S.; Swaminathan, M. Catal.
Commun. 2010, 11, 997–1002.
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C. W. Tetrahedron Lett. 2004, 45, 4873–4876.
19. Kaupp, G. In Organic Solid State Reactions: 2005; pp 95–183.
20. Kaupp, G. CrystEngComm 2006, 8, 794–804.
29. Data for 11-methyldibenzo[a,c]phenazine: yield (1.78 g, 95%), all the analyses
were purchased on the crude product. Mp: 218–220 °C 1H NMR dH(200 MHz;
(CD3)2SO; Me4Si): 9.30 ppm (2H, d, 7.4 Hz, 4-H and 5-H), 8.83 ppm (2H, d, 8 Hz,
1-H and 8-H), 8.27 ppm (1H, d, 8.6 Hz, 9-H), 8.16 ppm (1H, s, 12-H), 7.98–
7.81 ppm (5H, m, 2-H, 3-H, 6-H and 7-H), 2.69 ppm (3H, s, 11-Me) MS–EI m/z:
294(M, 100%), 147(37), 146(21), 295(M+1, 19), 133(15), 293(Mꢀ1, 11).
m(KBr)/
21. Kaupp, G.; Schmeyers, J.; Boy, J. Tetrahedron 2000, 56, 6899–6911.
22. Kaupp, G.; Schmeyers, J.; Boy, J. Chemosphere 2001, 43, 55–61.
23. Kaupp, G. CrystEngComm 2009, 11, 388–403.
24. Rodriguez, B.; Bruckmann, A.; Rantanen, T.; Bolm, C. Adv. Synth. Catal. 2007,
349, 2213–2233.
25. Zefirov, N. S.; Sereda, G. A.; Volkov, V. P.; Tkachenko, S. E.; Zyk, N. V. Chem.
Heterocycl. Compd. 1996, 32, 577–579.
26. Yavari, I.; Mostafavi, H.; Tahmassebi, D.; Hekmat-Shoar, R. Monatsh. Chem.
1997, 128, 675–679.
cmꢀ1:3374 (N–H, w), 3060 and 3037 (C–H, sharp doublet, w); UV (DMSO):
maxima observed at 264, 286, 314, 380, 400 nm. Anal. Calcd for C21H14N2: C,
85.69; H, 4.79; N, 9.52. Found: C, 85.90 0,12; H, 4.74 0,09; N, 9.36 0,06.
Data for Dibenzo[a,c]phenazine: yield (1.77 g, >99%). Mp: 224 °C. All the
analyses were performed on the crude product. 1H NMR dH(200 MHz;
(CD3)2SO; Me4Si): 9.34 ppm (2H, dd, 7.6 Hz, 1.8 Hz, 4-H and 5-H), 8.86 ppm
(2H, dd, 7.7 Hz, 1.4 Hz, 1-H and 8-H), 8.4 ppm (2H, dd, 3.4 Hz, 6.6 Hz, 9-H and
12-H), 8.04 ppm (2H, dd, 3.4 Hz, 6.6 Hz, 10-H and 11-H), 7.99–7.83 ppm (4H,
m, 2-H, 3-H, 6-H and 7-H) MS–EI m/z: 280(M, 100%), 140(47), 281(M+1, 21),
27. Muddasir, H.; Lu, P.; Wang, Z. M.; Yang, S.-M.; Yang, B.; Wang, C.-L.; Ma, Y. G.
Chem. Res. Chinese universities 2009, 25, 950–956.
126(12); m
(KBr)/cmꢀ1: 3380 (N–H, br, w), 3059 and 3031 (C–H, sharp doublet,
w); UV (DMSO): maxima observed at 264, 284, 314, 378, 396 nm. Anal. Calcd
for C20H12N2: C, 85.69; H, 4.31; N, 9.99. Found: C, 85.78 0,15; H, 4.31 0,11;
N, 9.91 0,13.
28. General procedure: reactions are carried out in a vibrating ball-mill Pulverisette
0 (Fritsch, Germany) in 4 h with an agate single ball. The reactants were
introduced in equimolar ratio and in solid state (powder, flakes, etc.) under
atmospheric conditions (air at room temperature and pressure). The total mass
introduced in the ball-mill was 2 g, the vibration frequency was 50 Hz, and the
vibration amplitude was 2.5 mm. All chemicals were purchased from Aldrich
and were used without any additional treatment (the purities of the reactants
are technical grade and comprise of between 95% and 97% for each compound).
Data for 11,110-bidibenzo[a,c]phenazine: yield (0.61 g, 48%), Mp: not observed.
For analysis, the pure product was obtained after a chromatographic column
with toluene/dioxane 3:1 as the eluent. The product is difficult to solubilize
and DMF was used as a solvent for the column deposit to limit this one. 1H
NMR dH(200 MHz; (CD3)2SO; Me4Si): 9.53–9.26 ppm (4H, m, 4-H, 5-H and 40-H,
50-H), 8.85 ppm (4H, d, 7 Hz, 1-H and 10-H, 8-H and 80-H), 8.61–8.26 ppm (4H,
m, 9-H and 90-H, 12-H and 120-H), 8.00–7.80 ppm (10H, m, 2-H and 20-H, 3-H
1H NMR (200 MHz) spectra were recorded on
a BRUKER Advance 200
spectrometer with (CD3)2SO as the solvent which was obtained from Euriso-
topÒ and tetramethylsilane (TMS) as the internal standard at 298 K. GC–MS
spectra were obtained with a Q5050A Shimadzu spectrometer with CH2Cl2 as
the solvent and in EI mode. The injector temperature was 280 °C and this of the
detector: 300 °C. The column flow was 1.4 mL/min. We used the following
temperature program: 140 °C for 4 min then go to 160 °C by 30 °C/min for
4 min and go to 270 °C by 30 °C/min and stay 20 min.
and 30-H). The GC–MS measurements gave us none result of MS); (KBr)/cmꢀ1
m :
3381 (N–H, br, w), 3071 and 3023 (C–H, sharp doublet, w); UV (DMSO):
maxima observed at 266, 306, 422 nm. Anal. Calcd for C40H22N4: C, 86.00; H,
3.97; N, 10.03. Found: C, 86.29 0.49; H, 3.88 0,30; N, 9.82 0.48.
Data for dibenzo[f,h]pyrido[2,3-b]quinoxaline: yield (1.63 g, 88%) Mp: 213 °C. For
analysis, the pure product was obtained after a chromatographic column with
toluene/dioxane 3:1 as the eluent. The product is difficult to solubilize and
DMF was used as a solvent for the column deposit to limit this one. The product
after elimination of the column solvent was washed with water to eliminate
any DMF traces and after that filtrated and dried. 1H NMR dH(200 MHz;
(CD3)2SO; Me4Si): 9.37 ppm (1H, dd, 4.1 Hz, 1.8 Hz, 10-H), 9.34–9.24 ppm (2H,
m, 4-H and 5-H), 8.84 ppm (1H, d, 8.4 Hz, 12-H), 8.80 ppm (2H, dd, 8.5 Hz,
1.8 Hz, 8-H and 1-H), 8.03 ppm (1H, dd, 8.5 Hz, 4.0 Hz, 11-H), 7.98–7.82 ppm
(4H, m, 2-H, 3-H, 6-H and 7-H). MS–EI m/z: 281(M,100%), 280(Mꢀ1, 26),
Melting points were obtained on a Netzsch thermal Analysis system STA409.
The study was made from 30 °C to 500 °C with a step of 5° C/min.
UV spectra were recorded on HP8452A Diode Array spectrophotometer in
precision cell made of quartz suprasilÒ with DMSO as the solvent with an
approximate concentration of 3 ꢁ 10ꢀ3 g/L.
A Fourier Transform Infrared (FTIR) spectrometer from Perkin Elmer model
series 2000 was used in order to make the acquisition of the IR spectra in KBr
Pellets.
282(M+1, 21), 140(20). (KBr)/cmꢀ1: 3426 (N–H, br, w), 3071 and 3021 (C–H,
m
For microanalysis: a thermoquest NA2100 elemental analyzer was used. This
model was equipped with an autosampler AS2000.
XRD experiments were carried out on a X’Pert Pro system from Panalytical. To
determine if the reactions occurred, 1H NMR was used as an analytical
technique and DSC–TGA for melting point measurements.
sharp doublet, w); UV (DMSO): maxima observed at 262, 314, 390 nm. Anal.
Calcd for C19H11N3: C, 81.12; H, 3.94; N, 14.94. Found: C, 81.75 0,88; H,
4.20 0,29; N, 14.05 0,77.