3
5j
1
85
91
74
1.5
82
74
70
5d
5e
4
5k
5l
1.5
2
2
5f
a Reagents and conditions: 1-4 (1 mmol), EtOH, 80 ºC.
21. Single crystal X-ray data for 5b: C22H15Cl4N3O4, M = 527.17,
monoclinic system, space group P21/c, a = 11.309(2), b = 16.327(3), c
= 12.264(3) Å; β = 106.41(3) º; V = 2172.2(8) Å3, Z = 4, Dcalcd = 1.612
g cm-3, μ (Mo-Kα)= 0.376 mm-1, crystal dimension of 0.35×0.25×0.20
mm. The X-ray diffraction measurement was made on a STOE IPDS-II
diffractometer with graphite monochromated Mo-Kα radiation. The
structure was solved by using SHELXS. The Data reduction and
structure refinement was carried out with SHELXL using the X-
STEP32 crystallographic software package.BB The non-hydrogen atoms
were refined anisotropically by full matrix least-squares on F2 values
to final R1 = 0.0907, wR2 = 0.1495 and S = 0.965 with 302 parameters
using 3823 independent reflection (θ range = 2.49-24.99º). The
crystallographic information file has been deposited with the
Cambridge Data Centre, CCDC 1509896. X-STEP32 Version 1.07b,
Crystallographic Package; Stoe & Cie GmbH: Darmstadt, Germany,
2000.
In conclusion we have successfully synthesised various
benzo[g]imidazo[1,2-a]quinolinedione derivatives in excellent
yields via a catalyst free, four component reaction between 1,1-
bis(methylthio)-2-nitro
ethylene,
ethylenediamine,
1,3-
indandione and aromatic aldehydes.
References and notes
1. Alizadeh, A.; Rezvanian, A.; Deng, Y. Tetrahedron 2010, 66, 9933-
9937.
2. Butler, M. S. J. Nat. Prod. 2004, 67, 2141-2153.
3. Garuti, L.; Roberti, M.; Pizzirani, D. Mini-Reviews in Med. Chem.
2007, 7, 481-489.
4. Wen, L. R.; Sun, Q. C.; Zhang, H. L.; Li, M. Org. Biomol. Chem.
2013, 11, 781–786.
5. Krapcho, A. P.; Ellis, M. Arkivoc 2000, i, 43-50.
6. Boger, D.L.; Hong, J.; Hikota, M.; Ishida, M. J. Am. Chem. Soc. 1999,
121, 2471-2477.
Supplementary Material
7. Jakeman, D. L.; Bandi, S.; Graham, C. L.; Reid, T. R.; Wentzell, J. R.;
Douglas, S. E. Antimicrob. Agents Chemother. 2009, 53, 1245–1247.
8. Mohammadi, A. A.; Taheri, S.; Amouzegar, A. J. Heterocyclic Chem.
2016, 53, 805-808.
Experimental procedure and spectral data (copies of 1H, 13C
NMR, IR and mass spectra of products, and crystallographic data
for 5b) can be found at http://.
9. Sarkar, R.; Mukhopadhyay, C. Tetrahedron Lett. 2014, 55, 2618–2624.
10. Toure, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439–4486.
11. Kazemi, B.; Javanshir, S.; Maleki, A.; Safari, M.; Khavasi, H. M.
Tetrahedron Lett. 2012, 53, 6977–6981.
12. Quiroga, J.; Trilleras, J.; Pantoja, D.; Abonía, R.; Insuasty, B.;
Nogueras, M.; Cobo, J. Tetrahedron Lett. 2010, 51, 4717–4719.
13. Ganem, B. Antimicrob. Agents Chemother. 2009, 42, 463-472.
14. Alizadeh, A.; Rezvanian, A. C. R. Chimie 2014, 17, 103–107.
15. Alizadeh, A.; Esmaili zand, H. R.; Saberi, V.; Mokhtari, J. Helv. Chim.
Acta. 2013, 96, 2240-2244.
16. Alizadeh, A.; Ghanbaripoura, R.; Ng, S. W. Helv. Chim. Acta. 2015,
98, 663-667.
17. Alizadeh, A.; Zohreh, N. Synlett 2012, 23, 428-432.
18. Alizadeh, A.; Moafi, L. Helv. Chim. Acta. 2015, 98, 546-551.
19. Chen, X.; Zhu, L.; Fang, L.; Yan, S.; Lin, J. RSC Adv. 2014, 4, 9926–
9934.
20. 4-nitro-5-phenyl-2,3-dihydrobenzo[g]imidazo[1,2-a]quinoline-
6,11(1H,5H)-dione (5a): Red powder: mp 238-240 oC (dec.), 0.306 g,
yield: 82%. IR (KBr) (max /cm-1): 3320 (NH), 1641 (C=O), 1480 (Ar),
1438 and 1357 (NO2), 1252 (C-N). MS (EI, 70 eV): m/z (%) = 373
(M+, 13), 340 (23), 327 (48), 296 (100), 250 (41), 193 (14), 139 (21),
105 (23), 77 (58), 51 (33), 41 (18). 1H NMR (300 MHz, DMSO):
3.83-3.89 (2H, m, CH2), 4.42-4.52 (1H, m, CH), 4.62-4.68 (1H, m,
CH), 5.45 (1H, s, CH), 7.09-7.1 (1H, m, 1CH of Ar), 7.18-7.23 (2H, m,
3
2CH of Ar), 7.32 (2H, d, JHH=7.5 Hz, 2CH of Ar), 7.78-8.01 (4H, m,
4CH of Naph.), 9.67 (1H, s, NH). 13C NMR (75 MHz, DMSO): 38.3
(CH), 44.6 (CH2NH), 48.6 (CH2N), 106.6 (C-NO2), 122.9, 125.7,
126.7, 127.1, 128.5, 128.7, 131.3, 131.4, 134.1, 135.0, 139.0, 143.6,
152.7 (C=C-NO2), 180.1 (C=O), 181.3 (C=O).