Paper
RSC Advances
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4
,4 -(1,3-phenylene)bis(2-(methylamino)-3-nitropyrano[3,2-
atom economy, environmental friendliness, simple operational
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c]chromen-5(4H)-one) (7a). White solid: mp: 312–314 C, yield: process and the non-chromatographic purication of products.
.541 g (87%). IR (KBr) (nmax/cm ): 3610, 1729, 1674, 1458, This study has shown that the experimental results are in good
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(
364, 1266, 1160. MS (EI, 70 eV): m/z (%) ¼ 256 (6), 200 (12), 136 agreement with the predicted values, and the model success-
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11), 96 (13), 81 (46), 69 (100). H NMR (300 MHz, DMSO-d
6
): fully can be used to predict the synthesis of such derivatives.
d 3.16–3.29 (12H, m, 4CH ), 5.03 (4H, s, 4CH), 7.13–8.02 (24H, Further studies on the synthetic application and physical
3
1
3
m, Ar), 10.25–10.40 (4H, m, 4NH). C NMR (62 MHz, DMSO-d6): properties examination are currently ongoing.
d 30.1 (4NHCH ), 38.4 (4CH), 108.2, 109.0, 113.9, 118.0, 124.1,
3
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26.5, 128.2, 129.3, 129.5, 134.6, 142.6, 153.4, 158.3, 160.5.
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Conflicts of interest
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,4 -(1,4-phenylene)bis(2-(methylamino)-3-nitropyrano[3,2-
ꢀ
c]chromen-5(4H)-one) (7b). White solid: mp: 325–327 C, yield:
The authors declare no competing nancial interest.
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0.566 g (91%). H NMR (300 MHz, DMSO-d
6
): d 3.25–3.32 (12H,
m, 4CH ), 5.02 (4H, s, 4CH), 7.19–8.02 (24H, m, Ar), 10.30–10.35
3
1
3
(
3
1
4H, m, 4NH). C NMR (62 MHz, DMSO-d ): d 30.1 (4NCH ), Acknowledgements
6
3
8.3 (4CH), 109.2, 118.0, 124.2, 126.4, 129.5, 134.5, 141.4, 153.5,
We acknowledge the nancial support of this research from
Imam Khomeini International University. We thank the Iran
National Science Foundation (No. 97021367) for nancial
support.
58.3, 160.5.
0
4,4 -(1,4-phenylene)bis(2-(ethylamino)-3-nitropyrano[3,2-c]
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chromen-5(4H)-one) (7c). White solid: mp: 290–292 C, yield:
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8
4
.533 g (82%). MS (EI, 70 eV): m/z (%) ¼ 256 (7), 137 (15), 97 (38),
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1 (73), 69 (100). H NMR (300 MHz, DMSO-d
6
): d 1.30 (12H, t,
CH ), 3.70–3.85 (8H, m, 4CH NH), 5.02 (4H, s, 4CH), 7.06–7.93
3
2
Notes and references
1
3
(24H, m, Ar), 10.43 (4H, s, 4NH). C NMR (62 MHz, DMSO-d6):
d 16.5 (4CH ), 38.3 (4CH), 38.5 (4CH ), 104.6, 108.1, 109.1, 114.1,
1 A. Aydar, Utilization of Response Surface Methodology in
Optimization of Extraction of Plant Materials, in Statistical
Approaches with Emphasis on Design of Experiments Applied
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One, 2018, 13, 1–14.
3
2
1
1
16.8, 118.1, 121.3, 124.0, 125.6, 126.4, 127.9, 129.0, 129.5,
30.5, 132.2, 134.5, 139.0, 141.4, 153.5, 157.8, 160.6, 179.2.
0
4
,4 -(1,4-phenylene)bis(3-nitro-2-propylaminopyrano[3,2-c]
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chromen-5(4H)-one) (7d). White solid: mp: 297–299 C, yield:
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4
5
.603 g (89%). H NMR (300 MHz, DMSO-d
CH ), 1.70–1.80 (8H, m, 4CH ), 3.65–3.80 (8H, m, 4CH
.03 (4H, s, 4CH), 7.05–7.98 (24H, m, Ar), 10.44 (4H, s, 4NH).
6
): d 0.90 (12H, t,
3
2
2
NH),
1
3
C
NMR (62 MHz, DMSO-d ): d 12.6 (4CH ), 24.2 (4CH ), 37.3
6
3
2
(
4CH), 44.8 (4CH NH), 104.6, 108.1, 109.1, 114.1, 116.8, 118.1,
2
1
1
21.3, 123.9, 125.6, 126.5, 127.9, 129.0, 129.5, 132.2, 134.5,
5 H. Tang, Q. Xiao, H. Xu and Y. Zhang, Org. Process Res. Dev.,
2013, 17, 632–640.
6 N. P. T. Nhan, T. T. Hien, L. T. H. Nhan, P. N. Q. Anh,
L. T. Huy, N. T. C. Trinh, D. T. Nguyen and L. G. Bach,
Metallurgy Technology and Materials VI, Solid State
Phenomena, 2018, 279, pp. 235–239.
41.4, 153.4, 157.9, 160.6, 169.0.
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,4 -(1,4-phenylene)bis(2-(isopropylamino)-3-nitropyrano
ꢀ
[
3,2-c]chromen-5(4H)-one) (7e). White solid: mp: 313–315 C,
yield: 0.576 g (85%). H NMR (300 MHz, DMSO-d ): d 1.30–1.40
24H, d, 8CH ), 4.45–4.60 (4H, m, 4CHNH), 5.02 (4H, s, 4CH),
6
(
3
1
3
7.19–7.95 (24H, m, Ar), 10.10–10.25 (4H, m, 4NH). C NMR (62
7 H. V. Srikanth, J. Venkatesh and S. Godiganur, Biofuel, 2018,
3, 1–11.
MHz, DMSO-d ): d 23.8 (8CH ), 38.2 (4CH), 46.4 (4CHNH),
6
3
1
1
04.6, 114.1, 116.8, 118.1, 121.5, 124.2, 125.6, 127.9, 129.0,
29.6, 130.7, 132.2, 134.6, 153.4, 153.9, 157.4, 160.6, 169.0.
8 M. A. Bezerra, R. E. Santelli, E. P. Oliveira, L. S. Villar and
L. A. Escaleira, Talanta, 2008, 76, 965–977.
9
T. A. Wani, A. Ahmad, S. Zargar, N. Y. Khalil and
I. A. Darwish, Chem. Cent. J., 2012, 6, 134–142.
Conclusion
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0 H. Aslani, R. Nabizadeh, S. Nasseri, A. Mesdaghinia,
M. Alimohammadi, A. H. Mahvi, N. Rastkari and
S. Nazmara, Desalin. Water Treat., 2016, 57, 25317–25328.
In summary, a simple and catalyst free method for the synthesis
0
of
4,4 -(1,4-phenylene)bis(2-(alkylamino)-3-nitro-4H-benzo[g]
0
chromene-5,10-dione) and 4,4 -(1,4-phenylene)bis(2-(alkyla- 11 J. Palaniraja, S. M. Roopan and G. M. Rayalu, RSC Adv., 2016,
mino)-3-nitropyrano[3,2-c]chromen-5(4H)-one) derivatives was
reported for the rst time. These compounds are obtained from 12 Y. He, J. Cai and Y. Zhang, J. Chem. Eng. Mater. Sci., 2017, 5,
a one-pot, multi-component reaction between various amines, 155–167.
,1-bis(methylthio)-2-nitroethene, terephthalaldehyde or iso- 13 L. M. Ramos, M. O. Rodrigues and B. A. D. Neto, Org. Biomol.
6, 24610–24616.
1
phthalaldehyde, and 2-hydroxy-1,4-naphthoquinone or 4-
Chem., 2019, 17, 7260–7269.
ꢀ
hydroxycoumarin in EtOH/H O (85 : 15) at 89 C. Aer optimi- 14 S. Samai, G. C. Nandi, R. Kumar and M. S. Singh, Tetrahedron
2
zation of reaction conditions by response surface methodology
Lett., 2009, 50, 7096–7098.
(RSM) all the products could be obtained in good yields (from 15 J. Wiemann, L. Fischer, J. Kessler, D. Strohl and R. Csuk,
75% to 91%). The key advantages of this new synthetic route are
Bioorg. Chem., 2018, 81, 567–576.
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RSC Adv., 2019, 9, 39466–39474 | 39473