1
734
A. R. Karimi et al.
PAPER
4
c
14
–
1
–1
IR (KBr):3429, 3344, 3180, 2204, 1716, 1672, 1606, 1361 cm .
IR (KBr): 3450, 3319, 2222, 1728, 1637, 1579 cm .
1
1
H NMR (300 MHz, DMSO-d ): d = 4.96–4.98 (ABq, 2 H, CH ),
H NMR (300 MHz, DMSO-d ): d = 7.48–8.37 (m, 12 H, NH and
6
2
6
2
6
7
.79 (t, J = 7.70 Hz, 1 H ), 7.00–7.02 (t, J = 7.42 Hz, 1 H ),
10 Harom).
arom
arom
.18–7.34 (m, 5 Harom), 7.46–7.56 (m, 4 Harom), 7.76–7.81 (m, 2
Harom), 7.79 (s, 2 H, NH ), 7.96–7.99 (dd, J = 7.90, 1.41 Hz, 1 Harom).
2
Acknowledgment
4
d
We gratefully acknowledge the financial support from the Research
Council of Arak University.
–
1
IR (KBr):3444, 3304, 3170, 2208, 1713, 1675, 1606, 1361 cm .
1
H NMR (300 MHz, DMSO-d ): d = 3.24 (s, 3 H, CH ), 7.05–7.13
m, 2 H ), 7.32–7.40 (m, 2 H ), 7.53–7.62 (m, 2 H ), 7.75–
6
3
(
arom arom arom
3
7
.80 (m, 3 H, NH and 1 H ), 7.97 (d, J = 7.85 Hz, 1 Harom).
References
2
arom
(
1) Foye, W. O. Principal di Chemico Farmaceutica; Piccin:
Padova (Italy), 1991, 416.
2) Singh, K.; Singh, J.; Singh, H. Tetrahedron 1996, 52, 14273.
6
a
–
1
IR (KBr): 3405, 3308, 3173, 2198, 1720, 1676, 1608, 1356 cm .
(
1
H NMR (300 MHz, DMSO-d ): d = 4.95 (ABq, 4 H, CH ), 6.79–
(3) Wang, X. S.; Shi, D. Q.; Tu, S. T.; Yao, C. S. Synth.
Commun. 2003, 33, 119.
(4) Abe, Y.; Ebara, H.; Okada, S.; Akaki, R.; Horii, T.; Nakao,
R. Dyes Pigm. 2002, 52, 23.
6
2
6
7
.82 (d, J = 7.90 Hz, 2 H ), 6.98–7.02 (t, J = 6.70 Hz, 2 H ),
.19–7.24 (t, J = 8.20 Hz, 3 Harom), 7.31–7.34 (d, J = 7.39 Hz, 2
arom arom
Harom), 7.43 (s, 4 H, NH ), 7.51–7.59 (m, 4 Harom), 7.78 (s, 5 Harom),
7
2
.96–7.99 (d, J = 8.03 Hz, 2 Harom).
(5) Glover, V.; Halket, J. M.; Watkins, P. J.; Clow, A.;
1
3
Goodwin, B. L.; Sandler, M. J. Neurochem. 1998, 51, 656.
C NMR (75 MHz, DMSO-d ): d = 43.70, 47.82, 57.17, 101.58,
6
(
(
6) Kumar, R.; Bansal, R. C.; Mahmood, A. Biog. Amines 1993,
, 281.
1
1
1
09.67, 112.88, 117.168, 117.52, 123.26, 123.45, 124.52, 125.55,
27.68, 129.52, 132.72, 133.14, 134.28, 135.36, 143.17, 152.53,
55.81, 158.88, 159.09, 176.42.
9
7) Medvedev, A. E.; Clow, A.; Sandler, M.; Glover, V.
Biochem. Pharmacol. 1996, 52, 385.
(8) (a) Bhattacharya, S. K.; Glover, V.; McIntyre, I.; Oxenkrug,
Anal. Calcd for C H N O : C, 70.58; H, 3.46; N, 10.29. Found: C,
7
4
8
28
6
8
1.08; H, 3.28; N, 10.78.
G.; Sandler, M. Neurosci. Lett. 1982, 92, 218.
(
b) Bhattacharya, S. K.; Mitra, S. K.; Acharya, S. B.
6
b
J. Psychopharmacol. 1991, 5, 202.
9) Sundberg, R. J. The Chemistry of Indoles; Academic Press:
New York, 1996.
–
1
IR (KBr):3427, 3342, 3115, 2198, 1716, 1674, 1606, 1359 cm .
(
1
H NMR (300 MHz, DMSO-d ): d = 4.96 (ABq, 4 H, CH ), 6.76 (s,
6
2
2
1
H
), 7.09–7.15 (m, 3 H ), 7.41 (s, 4 H, NH ), 7.55–7.96 (m,
(10) Da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem.
arom
arom
2
3 Harom).
Soc. 2001, 12, 273.
(
11) Abdel-Rahman, A. H.; Keshk, E. M.; Hanna, M. A.;
El-Bady, Sh. M. Bioorg. Med. Chem. 2004, 12, 2483.
12) (a) Kornet, M. J.; Thio, A. P. J. Med. Chem. 1976, 19, 892.
1
3
C NMR (75 MHz, DMSO-d ): d = 43.71, 47.94, 56.54, 100.92,
6
1
1
1
11.59, 113.07, 115.36, 117.19, 117.46, 123.30, 125.52, 127.70,
32.21, 133.21, 134.29, 135.02,136.34, 137.64, 142.46, 152.60,
56.15, 159.07, 159.19, 176.08.
(
(
b) Hilton, S. T.; Ho, T. C.; Pljevalijcic, G.; Jones, K. Org.
Lett. 2000, 2, 2639. (c) Kumar, R. S.; Rajesh, S. M.;
Perumal, S.; Banerjee, D.; Yogeeswari, P.; Sriram, D. Euro.
J. Med. Chem. 2009, 1.
Anal. Calcd for C H Br N O : C, 59.16; H, 2.69; N, 8.62. Found:
C, 58.48; H, 2.83; N, 8.33.
4
8
26
2
6
8
(
13) Rahman, A.; Silva, W. S. J.; Alvi, K. A.; De Silva, K. T. D.
Spiro-2-amino-4H-pyrans 12, 13, and 14
Phytochemistry 1987, 26, 865.
The spiro-2-amino-4H-pyrans 12, 13, and 14 were prepared as
described for the above products by three-component reaction of
ninhydrin (9; 1 mmol), 9,10-phenanthroquinone (10, 1 mmol), or
acenaphthenequinone (11, 1 mmol) with 2 (1 mmol) and 3 (1
mmol).
(14) Rahman, A.; Qureshi, M. M.; Muzaffar, A.; De Silva, K. T.
D. Heterocycles 1988, 27, 725.
(15) Harada, M.; Ozaki, Y. Chem. Pharm. Bull. 1978, 26, 48.
(
16) (a) Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.;
White, A. H. Tetrahedron 2007, 63, 1191. (b) Marti, C.;
Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 11505.
(c) Feldman, K. S.; Karatjas, A. G. Org. Lett. 2006, 8, 4137.
1
2
–
1
IR (KBr):3394, 3321, 3189, 1714, 1672, 1359 cm .
(17) (a) Elinson, M. N.; Ilovaisky, A. I.; Dorofeev, A. S.;
Merkulova, V. M.; Stepanov, M. O.; Miloserdov, F. M.;
Ogibin, Yu. N.; Nikishin, G. I. Tetrahedron 2007, 63,
1
H NMR (300 MHz, DMSO-d ): d = 7.55–7.62 (m, 3 Harom), 7.80–
6
7
2
.88 (m, 2 H ), 7.92–7.97 (m, 2 H ), 8.06 (s, 1 Harom), 8.13 (s,
arom arom
1
0543. (b) Wang, L.-M.; Jiao, N.; Qiu, J.; Yu, J.-J.; Liu,
J.-Q.; Guo, F.-L.; Liu, Y. Tetrahedron 2010, 66, 339.
c) Zhu, S.-L.; Jia, S.-J.; Zhang, Y. Tetrahedron 2007, 63,
365. (d) Dabiri, M.; Bahramnejad, M.; Baghbanzadeh, M.
H, NH2).
1
3
C NMR (75 MHz DMSO-d ): d = 52.74, 53.21, 100.16, 112.37,
6
(
9
1
1
1
16.94, 117.32, 117.49, 123.00, 124.12, 125.53, 125.91, 126.79,
34.75, 135.68, 137.83, 140.94, 152.66, 157.20, 160.04, 160.22,
99.30.
Tetrahedron 2009, 65, 9443.
(
18) (a) Karimi, A. R.; Behzadi, F.; Amini, M. M. Tetrahedron
Lett. 2009, 49, 5393. (b) Karimi, A. R.; Pashazadeh, R.
Synthesis 2010, 437. (c) Karimi, A. R.; Alimohammadi, Z.;
Amini, M. M. Mol. Diver. 2010, in press.
1
3
–
1
IR (KBr): 3400, 3321, 2212, 1737, 1606, 1541, 1413 cm .
1
H NMR (300 MHz, DMSO-d ): d = 7.37–7.97 (m, 12 Harom), 8.86
(19) Azizian, J.; Mohammadi, A. A.; Karimi, A. A.;
6
(
s, 2 H, NH ).
Mohammadizadeh, M. R. J. Org. Chem. 2005, 70, 350.
2
(
20) Aderemi, B. O.; Hameed, B. H. J. Mol. Catal. A: Chem.
Anal. Calcd for C H N O : C, 74.64; H, 3.37; N, 6.70. Found: C,
2
6
14
2
4
2009, 370, 54.
7
4.29; H, 3.46; N, 6.62.
Synthesis 2010, No. 10, 1731–1735 © Thieme Stuttgart · New York