RSC Advances
Paper
1
3
6
ppm. C NMR (62.9 MHz, DMSO-d ) 195.1(C]O), 178.2(C]O),
References
1
1
3
3
66.1(C), 158.7(C), 142.0(C), 134.6(C), 128.5(CH), 123.3(CH),
21.8(CH), 117.4(CH), 112.9(CN), 109.2(C), 57.6(C), 46.9(C),
1 B. Das, K. Venkateswarlu, H. Holla and M. Krishnaiah, J. Mol.
Catal. A: Chem., 2006, 253, 107.
2 A. Shaabani, A. Rahmati and Z. Badri, Catal. Commun., 2008,
9, 13.
3 C. L. Carnes and K. J. Klabunde, J. Mol. Catal. A: Chem., 2003,
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4 V. Biju and M. Abdul Khadar, Mater. Sci. Eng., A, 2001, 304,
814.
ꢁ
1
6.4(CH ), 26.8(CH ), 19.8(CH ). IR (KBr, cm ) 3352, 3295,
2
2
2
175, 2952, 2204, 1713, 1655, 1352, 1216, 1076. Anal. calcd for
: C, 66.44; H, 4.26; N, 13.67%. Found: C, 66.42; H,
.31; N, 13.72%.
-Amino-7,7-dimethyl-2 ,5-dioxo-5,6,7,8-tetrahydrospiro[chro-
17 13 3 3
C H N O
4
0
2
0
mene-4,3 -indoline]-3-carbonitrile (compound 12, Table 3).
ꢀ
1
White solid, mp > 250 C. H NMR (250 MHz, DMSO-d ): 1.00
6
(
3H, s, CH ), 1.1 (3H, s, CH ), 2.08–2.12 (2H, m, CH ), 2.56 (2H,
5 Y. Wang, J. Zhu, X. Yang, L. Lu and X. Wang, Thermochim.
Acta, 2005, 437, 106.
6 R. J. Sundberg, The Chemistry of Indoles, Academic Press, New
York, 1996.
7 K. C. Joshi and P. Chand, Biologically active indole
derivatives, Pharmazie, 1982, 37, 1.
8 A. H. Abdel-Rahman, E. M. Keshk, M. A. Hanna and S. M. El-
Bady, Bioorg. Med. Chem., 2004, 12, 2483.
9 T. H. Kang, K. Matsumoto, M. Tohda, Y. Murakami,
H. Takayama, M. Kitajima, N. Aimi and H. Watanabe, Eur.
J. Pharmacol., 2002, 444, 39.
3
3
2
m, CH ), 6.70 (d, 1H, J ¼ 7.4 Hz, Ph), 6.88 (t, 1H, J ¼ 7.4 Hz, Ph),
2
7
2
1
1
1
3
3
.10 (d, 1H, J ¼ 7.4 Hz, Ph), 7.22 (t, 1H, J ¼ 7.4 Hz, Ph), 7.35 (s,
1
3
2 6
H, NH ), 10.65 (s, 1H, NH). C NMR (62.9 MHz, DMSO-d )
95.3(C]O), 178.5(C]O), 166.58(C), 159.20(C), 152.4(C),
42.48(C), 134.83(CH), 128.59(CH), 123.4(CH), 122.16(CH),
17.76(C), 112.22(CN), 109.7(C), 57.96(C), 50.45(CH
2
), 47.23(C),
ꢁ
1
2.35(CH ), 28.01(CH ), 27.1(CH ). IR (KBr, cm ): 3376, 3312,
2
3
3
ꢁ
1
144, 2928, 2196, 1724, 1656, 1348, 1224, 1056 cm . Anal. calcd
for C H N O : C, 68.05; H, 5.11; N, 12.53%. Found: C, 67.86;
H, 5.14; N, 12.65%.
1
9
17 3 3
0
2
-Amino-2 ,5-dioxo-5,6-dihydro-spiro[pyrano[3,2-c]quinoline- 10 J. Leclercq, M. C. De Pauw Gillet, R. Bassleer and L. Angenot,
0
4
,3 -indoline]-3-carbonitrile (compound 1, Table 4). White solid,
J. Ethnopharmacol., 1986, 15, 305.
ꢀ
1
mp > 250 C. H NMR (250 MHz, DMSO-d
6
): 6.83 (1H, d, J ¼ 7.6 11 (a) J. Ma and S. M. Javaniside, Chem. Commun., 2004, 1190;
Hz, Ph), 6.92 (1H, t, J ¼ 7.6 Hz, Ph), 7.17 (1H, d, J ¼ 7.2 Hz, Ph),
(b) R. Y. Guo, Z. M. An, L. P. Mo, R. Z. Wang, H. X. Liu,
S. X. Wang and Z. H. Zhang, ACS Comb. Sci., 2013, 15, 557.
7
.32 (1H, d, J ¼ 7.6 Hz, Ph), 7.44 (1H, t, J ¼ 7.6 Hz, Ph), 7.48 (1H,
t, J ¼ 8.2 Hz, Ph), 7.52 (1H, d, J ¼ 8.4 Hz, Ph), 7.53 (2H, s, NH ), 12 S. Pepeljnjak, I. Jalsenjak and D. Maysinger, Pharmazie,
2
1
3
7
.95 (1H, d, J ¼ 8.2 Hz, Ph), 10.65 (1H, s, NH). C NMR (62.9
1982, 37, 864.
MHz, DMSO-d ) 177.4(C]O), 158.9(C]O), 155.7(C), 155.5(C), 13 B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo,
6
1
1
1
3
52.4(CH), 142.6(CH), 134.1(CH), 133.5(CH), 129.38(C), 125.4(C),
R. M. Freidinger, W. L. Whitter, G. F. Lundell, D. F. Veber,
P. S. Andersons and R. S. Chang, J. Med. Chem., 1988, 31,
2235.
24.5(CH), 123.12(CH), 122.52(CH), 117.42(CH), 117.09(C),
ꢁ1
12.9(CN), 109.9(C), 101.9(C), 70.2(C), 57.5(C). IR (KBr, cm ):
415, 3241, 3260, 2218, 1719, 1679, 1623, 1581; Anal. calcd for 14 L. L. Andreani and E. Lapi, Boll. Chim. Farm., 1960, 99, 583.
C H N O : C, 67.23; H, 3.10; N, 11.76%. Found: C, 67.39; H, 15 L. Bonsignore, G. Loy and D. Secci, Eur. J. Med. Chem., 1993,
2
0
11 3 4
3.12; N, 11.65%.
28, 517.
1
1
6 C. J. Li, Chem. Rev., 2005, 105, 3095.
7 F. Bazi, H. Badaoui, S. Tamani, S. Sokori, A. Solhy,
D. J. Macquarrie and S. Sebti, Appl. Catal., A, 2006, 211, 301.
8 M. A. Nasseri, F. Ahrari and B. Zakerinasab, RSC Adv., 2015,
5, 13901.
Conclusions
In summary, an efficient protocol for the preparation of spi-
1
0
rocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3 -oxindole and
dihydro[pyrano[3,2-c]quinoline]-4,3-indoline derivatives was 19 M. A. Nasseri, B. Zakerinasab and M. M. Samieadel, RSC
described. The procedure offers several advantages including
Adv., 2014, 4, 41753.
the cheapness and the availability of the catalyst, mild reaction 20 M. A. Nasseri, S. A. Alavi and B. Zakerinasab, J. Iran. Chem.
conditions and high yields of the products as well as simple
experimental and isolation procedures. All these, make this
protocol a useful and an attractive procedure for the synthesis
of oxindole and indoline derivatives.
Soc., 2013, 10, 21.
1 M. A. Nasseri and M. Salimi, Lett. Org. Chem., 2013, 10, 164.
2 M. A. Nasseri and S. M. Sadeghzadeh, J. Iran. Chem. Soc.,
2
2
2014, 11, 27.
Acknowledgements
We gratefully acknowledge the support of this work by the Bir-
jand University research council.
26520 | RSC Adv., 2015, 5, 26517–26520
This journal is © The Royal Society of Chemistry 2015