JOURNAL OF CHEMICAL RESEARCH 2015 317
1
85.0, 36.8, 27.2, 20.2 ppm. Anal. calcd for C17H12IN3O3 (433.2): C, 47.13; H,
2.79; N, 9.70; found: C, 47.18; H, 2.61, N, 9.60%.
1475, 1345, 1220, 1160, 1055, 805; H NMR (500 MHz, DMSO-d6): δ
10.49 (1H, s, NH), 7.27 (2H, s, NH2), 7.15 (1H, d, J = 7.53 Hz, ArH), 7.06
(1H, s, ArH), 6.76 (1H, d, J = 7.78 Hz, ArH), 2.55 (1H, d, J = 17.20 Hz, –
CH2–C=O) , 2.48 (1H, d, J = 17.20 Hz, –CH2–C=O), 2.11 (2H, s, –CH2–),
0.96 (6H, s, 2CH3) ppm.
2-Amino-5´-chloro-2´,5-dioxo-5,6,7,8-tetrahydrospiro[chromen-4,3´-
indoline]-3-carbonitrile (4j): Cream powder; IR (KBr) (νmax/cm-1): 3350,
3300, 3150, 2950, 2199, 1718, 1670, 1647, 1618, 1595, 1475, 1210, 1190,
1070, 830, 805, 722; 1H NMR (DMSO-d6, 400 MHz): δ 10.56 (1H, s, NH),
7.32 (2H, s, NH2), 7.19 (1H, d, J = 7.2 Hz, ArH), 7.16 (1H, s, ArH), 6.81 (1H,
d, J = 7.6 Hz, ArH), 2.66 (2H, s, br., –CH2–C=O), 2.26 (2H, s, br., –CH2–),
1.95 (2H, s, br., –CH2–CH2– CH2–) ppm.
2-Amino-5´-methoxy-7,7-dimethyl-2´,5-dioxo-5,6,7,8-tetra-
hydrospiro[chromen-4,3´-indoline]-3-carbonitrile (4c): White powder;
IR (KBr) (νmax/cm-1): 3390, 3300, 3250, 3200,3050, 3020, 2960, 2200,
1670, 1650, 1599 1480, 1460, 1358, 1220, 1160, 1045, 800, 742. 1H NMR
(500 MHz, DMSO-d6): δ 10.16 (1H, s, NH), 7.17 (2H, s, NH2), 6.66 (2H,
s, ArH), 6.56 (1H, s, ArH), 3.62 (3H, s, OCH3), 2.46 (2H, s, –CH2–C=O),
2.12 (1H, d, J = 16.0 Hz, –CH2–), 2.07 (1H, d, J = 16.0 Hz, –CH2–), 0.99,
0.98 (6H, s, 2CH3) ppm. 13C NMR (125 MHz, DMSO-d6), δ 195.7, 178.8,
165.0, 159.6, 155.8, 136.6, 136.3, 118.2, 113.4, 111.6, 111.0, 110.4, 56.2,
50.9, 48.1, 32.8, 28.4, 28.0 ppm. Anal. calcd for C20H19N3O4 (365.38): C,
65.74; H, 5.24; N, 11.50; found: C, 65.88; H, 5.11, N, 11.37%.
2-Amino-5´-methoxy-2´,5-dioxo-5,6,7,8-tetrahydrospiro[chromen-
4,3´-indoline]-3-carbonirile (4d): White powder; IR (KBr) (νmax/cm-1):
3400, 3300, 3220, 3180, 3002, 2200, 1700, 1680, 1650, 1600, 1500, 1460,
1210, 1190, 1080, 1010, 856, 818, 780. 1H NMR (400 MHz, DMSO-d6), δ
10.24 (1H, s, NH), 7.23 (2H, s, NH2), 6.72–6.66 (3H, m, ArH), 3.68 (3H, s,
OCH3), 3.39 (2H, s, –CH2–C=O), 2.24 (2H, s, –CH2–), 1.94 (2H, s, –CH2–
CH2– CH2–) ppm. 13C NMR (100 MHz, DMSO-d6): δ 195.5, 178.5, 166.5,
159.1, 155.4, 136.3, 135.8, 117.9, 113.0, 112.3, 110.8, 109.9, 55.8, 36.9, 27.2,
20.2 ppm. Anal. calcd for C18H15N3O4 (337.33): C, 64.09; H, 4.48; N, 12.46;
found: C, 64.28; H, 4.35, N, 12.58%.
The authors are grateful to the Research Council of University of
Guilan for the financial support of this research work.
Received 3 April 2015; accepted 8 May 2015
Published online: 4 June 2015
References
1
W. J. Houlihan, W. A. Remers and R. K. Brown, Indoles: Part I, Wiley. New
York, 1992.
2-Amino-7,7-dimethyl-2´,5-dioxo-5,6,7,8-tetrahydrospiro
[chromen-
2
3
4
R. J. Sundberg, The chemistry of indoles. Academic, New York, 1996.
K. C. Joshi and P. Chand, Pharmazie, 1982, 37, 1.
A. H. Abdel-Rahman, E. M. Keshk, M. A. Hanna and S. M. El-Bady, Bioorg.
Med. Chem., 2004, 12, 2483.
M. M. Khafagy, A. H. F. A. El-Wahas, F. A. Eid and A. M. El-Agrody,
T. H. Kang, K. Matsumoto, Y. Murakami, H. Takayama, M. Kitajima, N. Aimi
4,3´-indoline]-3-carbonitrile (4e): White powder; IR (KBr) (νmax/cm-1):
3380, 3300, 3140, 3020, 2950, 1708, 1680, 1650, 1600, 1345 (C-H bend,
CH3), 1220, 1160, 1050, 740. 1H NMR (500 MHz , DMSO-d6): δ 10.38
(1H, s, NH), 7.20 (2H, s, NH2), 7.14 (1H, t, J = 7.35 Hz, ArH), 6.98 (1H,
d, J = 7.0 Hz, ArH), 6.89 (1H, t, J = 7.21 Hz, ArH), 6.79 (1H, d, J = 7.54
Hz, ArH), 2.55 (2H, dd, J = 8.0 Hz, –CH2–C=O), 2.13 (2H, dd, J = 15.98
Hz, –CH2–), 1.03 (3H, s, CH3), 1.0 (3H, s, CH3) ppm. 13C NMR (125
MHz, DMSO-d6) : δ 195.7, 178.9, 165.0, 159.6, 142.9, 135.3, 129.0, 123.9,
122.5, 118.2, 111.7, 110.1, 50.9, 47.7, 32.8, 28.5, 27.9 ppm. Anal. calcd for
C19H17N3O3 (335.36): C, 68.05; H, 5.11; N, 12.53; found: C, 68.16; H, 5.27,
N, 12.64%.
5
6
7
8
9
T. Onishi, P. R. Sebahar and R. M. Williams, Tetrahedron, 2004, 60, 9503
T. Onishi, P. R. Sebahar and R. M. Williams, Org. Lett., 2003, 5, 3135.
11 P. B. Alper, C. Meyers, A. Lerchner, D. R. Siegel and E. M. Carreira, Angew.
2-Amino-7,7-dimethyl-5´-nitro-2´,5-dioxo-5,6,7,8-tetra-
hydrospiro[chromen-4,3´-indoline]-3-carbonitrile (4f): Yellow powder;
IR (KBr) (νmax/cm-1): 3460, 3350, 3100, 2200, 1722, 1680, 1650, 1595,
1480, 1460, 1510, 1345, 1360, 1210, 1180, 1050, 822, 740, 700; 1H NMR
(500 MHz, DMSO-d6): δ 11.14 (1H, s, NH), 8.11 (1H, d, J = 7.1 Hz, ArH),
7.92 (1H, s, ArH),7.41 (2H, s, NH2), 6.98 (1H, d, J = 7.4 Hz, ArH), 2.62
(1H, d, J = 17.4 Hz, –CH2–C=O) 2.48 (1H, d, J = 17.4 Hz, –CH2–C=O),
2.16(1H, d, J = 15.11 Hz, –CH2–), 2.10 (1H, d, J = 15.11 Hz, –CH2–), 0.99
(6H, s, 2CH3) ppm. C19H16N4O5 (380.36): C, 60.0; H, 4.24; N, 14.73; found:
C, 60.16; H, 4.12, N, 14.61%.
2-Amino-5´-nitro2´,5-dioxo-5,6,7,8-tetrahydrospiro[chromen-4,3´-
indoline]-3-carbonitrile (4g): Yellow powder; IR IR (KBr) (νmax/cm-1):
3460, 3350, 3198, 3060, 2200, 1740, 1719, 1678, 1650, 1620 (N–H bend),
1585, 1482, 1443, 1502, 1330, 1200, 1180, 1065, 822, 740, 720; 1H NMR
(400 MHz, DMSO-d6): δ 11.20 (1H, s, NH), 8.16 (1H, d, J = 8.0 Hz, ArH),
8.0 (1H, s, ArH),7.46 (2H, s, NH2),7.03 (1H, d, J = 8.4 Hz, ArH), 2.70 (2H,
s, br., –CH2–C=O), 2.26 (2H, s, br., –CH2–), 1.96 (2H, br. s, –CH2–CH2–
CH2–) ppm. C17H12N4O5 (352.08): C, 57.96; H, 3.43; N, 15.90; found: C,
57.65; H, 4.10, N, 15.60%.
2-Amino-1´-benzyl-7,7-dimethyl-2´,5-dioxo-5,6,7,8-tetra-
hydrospiro[chromen-4,3´-indoline]-3- carbonitrile (4h): White powder;
IR (KBr) (νmax/cm-1): 3380, 3305, 3180, 3020, 2920, 2200, 1708, 1680,
1662, 1598, 1482, 1350, 1220, 1200, 1055, 800, 770, 700; 1H NMR (500
MHz, DMSO-d6): δ 7.46, 7.45 (2H, s, NH2), 7.29–7.22 (5H, m, ArH), 7.09
(1H, t, J = 7.44 Hz, ArH), 7.05 (1H, d, J = 7.06 Hz, ArH), 6.92 (1H, t, J =
7.18 Hz, ArH), 6.65 (1H, d, J = 7.57 Hz, ArH), 4.88 (2H, AB quart., J =
16.14 Hz, –H2C– Ar), 2.60 (1H, d, J = 17.65 Hz, –CH2–C=O), 2.54 (1H, d,
J = 17.65 Hz, –CH2–C=O), 2.18 (1H, d, J = 15.97 Hz, –CH2–), 2.10 (1H, J
= 15.97 Hz, –CH2–), 1.02 (3H, s, CH3), 0.98 (3H, s, CH3) ppm.
12 S. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino and N. Rosen, J. Am.
13 T. Matsuura, L. E. Overman and D. J. Poon, J. Am. Chem. Soc., 1998, 120,
6500.
14 A. Ashimori, B. Bachand, L. E. Overman and D. J. Poon, J. Am. Chem. Soc.,
1998, 120, 6477.
16 M. N. Elinson, A. I. Ilovaisky and A. S. Dorofeev, V. M. Merkulova, N. O.
Stepanov, F. M. Miloserdov, Y. N. Ogibin and G. I. Nikishin, Tetrahedron,
2007, 63, 10543
17 S. L. Zhu, S. J. Ji and Y. Zhang, Tetrahedron, 2007, 63, 9365.
18 M. Dabiri, M. Bahraminejad and M. Baghbanzadeh, Tetrahedron, 2009, 65,
9443.
19 R. Sridha, B. Srinivas, S. Madhav, V. P. Reddy, Y. V. D. Lajeswar and K. R.
20 M. N. Elison, A. I. Ilovasiky, A. S. Dorofeev, V. M. Merkulova, N. O. Stepanov,
F. M. Miloserdov, Y. N. Ogibin and G. I. Nikishin, Tetrahedron, 2007, 63,
10543.
21 L. M. Wang, N. Jiao, J. J. Yu, J. Q. Liu, F. L. Guo and Y. Liu, Tetrahedron,
2010, 66, 339.
22 Y. Li, H. Chen, C. Shi, B. Shi and S. Ji, J. Comb. Chem., 2010, 12, 231.
24 24 T. J. Mason and J. P. Lorimer, Applied sonochemistry, the uses of power
ultrasound in chemistry and processing. Wiley VCH, Verlag GmbH, 2002.
25 A. Bazgir, S. Ahadi, R. Ghahremanzadeh, H.R. Khavasi and P. Mirzaei,
Ultrason. Sonochem., 2010, 17, 447
26 Z. H. Zhang, J. J. Li and T. S. Li, Ultrason. Sonochem., 2008, 15, 673.
27 M. Mamaghani, F. Shirini, N. O. Mahmoodi, A. Azimi-Roshan and H.
Hashemlou, J. Mol. Struct., 2013, 1051, 169.
28 R. Hossein nia, M. Mamaghani, K. Tabatabaeian, F. Shirini and M. Rassa,
Bioorg. Med. Chem. Lett., 2012, 22, 5956.
29 M. Mamaghani, A. Loghmanifar and R. Taati, Ultrason. Sonochem., 2011,
18, 45.
30 M. Nikpassand, M. Mamaghani, F. Shirini and K. Tabatabaeian, Ultrason.
Sonochem., 2010, 17, 301.
2-Amino-5´-chloro-7,7-dimethyl-2´,5-dioxo-5,6,7,8-tetrahydrospiro
[chromen-4,3´-indoline]-3-carbonitrile (4i): Cream powder, IR (KBr)
(νmax/cm-1): 3380, 3300,3155,3060, 2950, 2200, 1718, 1680, 1647, 1600,