Synthesis and Dynamic NMR Studies of New Podands of Dithiocarbamates Formed from Bis(naphthyl) Derivatives 667
–
1
1
7
(
3
4
7
96 cm ; H NMR (300 MHz, DMSO-d
6
); δ 1.17
K.; Hashizume, T.; Morishima, H. Bioorg Med Chem
001, 9, 1571–1578.
10] Scozzafava, A.; Mastrolorenzo, V.; Supuran, C. T.
Bioorg Med Chem Lett 2000, 10, 1887–1891.
11] Cao, S. L.; Feng, Y. P.; Jiang, Y. Y.; Liu, S. Y.; Ding,
G. Y.; Li, R. T. Bioorg Med Chem Lett 2005, 15, 1915–
1917.
2
t, J = 6.8 Hz, 12H), 3.01 (t, J = 5.4 Hz, 4H),
[
[
.57 (q, 4H), 3.88 (q, 4H), 4.04 (t, J = 5.5 Hz,
H),7.30–7.38 (m, 4H), 7.51 (t, J = 7.5 Hz, 2H),
13
.8–7.88 (m, 4H), 8.69 (d, J = 8.1 Hz, 2H) ppm;
C
NMR (300 MHz, DMSO-d
6
); δ 11.2, 12.3, 35.0, 46.4,
9.1, 67.2, 114.3, 115.9, 123.7, 125.1, 126.8, 128.2,
29.1, 129.7, 134.8, 156.0, 193.4 ppm; Anal. calcd
NO : C,61.04; H, 6.03; N, 4.19. Found:
[
[
12] Schonenberger, V. H.; Adam, A. Arzneim Forsch
4
1
(
Drug Res) 1964, 14, 1168.
13] Schonenberger, V. H.; Adam, A.; Adam, D. Arzneim
Forsch (Drug Res) 1966, 16, 734.
[14] Hogrth, G.; Rainford-Brent, E. J. C.; Richards, I., In-
org Chim Acta 2009, 362, 1361–1364.
15] Burke, J. T. R.; Bajwa, B. S.; Jacobsen, A. E.; Rice,
K. C.; Streaty, R. A. J Med Chem 1984, 27, 1570–
for C26
H19Cl
2
4
C,61.36; H, 5.87; N, 4.33.
,1 -Bis[2-(naphthalene-2-yl oxy)ethyl piperidine-
-carbodithioate]sulfide V
14 C; IR (KBr): 1430, 1266, 1240, 1226, 1054, 797
cm ; H NMR (300 MHz, DMSO-d ); δ 1.50–1.66
ꢂ
1
[
2
2
h
. Yield 91%, mp 213–
◦
1
574.
–
1
1
6
[
16] Walter, W.; Bode, K. D. Angew Chem, Int Ed Engl
1967, 6, 281–293.
[17] (a) Dunn, A. D.; Rudorf, W. D. Carbon Disulphide in
Organic Chemistry; Ellis Howard: Chichester, UK,
1989, 226; (b) Garin, J.; Melandz, E.; Merchain,
F. L.; Tejero, T.; Urid, S.; Ayestaron, J. Synthesis 1991,
(
m, 12H), 3.03 (t, J = 5.4Hz, 4H), 3.70 (s, br, 4H),
4
7
4
.038 (t, J = 5.4Hz, 4H), 4.16 (s, br, 4H), 7.25–
.39 (m, 4H), 7.52 (t, J = 8.4Hz, 2H), 7.85–7.92 (m,
13
H), 8.69 (d, J = 8.4Hz, 2H) ppm; C NMR (300
MHz, DMSO-d
6
); δ 23.4, 23.4, 25.1, 25.6, 35.0, 50.7,
2.4, 67.2, 114.4, 116.6, 123.7, 125.1, 126.8, 128.2,
29.1, 129.7, 134.8, 156.0, 193.2 ppm; Anal. calcd
NO : C, 62.39; H, 5.82; N, 4.04. Found:
1
47–151; (c) Lee, A. W. M.; Chan, W. H.; Wong, H. C.;
5
1
Wong, M. S. Synth Commun 1989, 19, 547–552; (d)
Degani, I.; Fochi, R. Synthesis 1978, 365–368.
[
18] (a) Chen, D. J.; Chen, V. J. Chem Res (S) 2000, 352;
for C26
H19Cl
2
4
(
2
1
b) Yan, V.; Chen, V. Synth Commun 1999, 29, 2875–
880; (c) Chen, Z. C.; Jin, Y. Y.; Stang, V. J. Org Chem
987, 52, 4117–4118.
C, 62.03; H, 5.72; N, 4.37.
N,N-Bis[2(1-methylenaphthalene-yl oxy)ethyl di-
ethylamine-2-carobodithioate]sulfide V
mp 203–204 C; IR (KBr): 1503, 1423, 1268, 1230,
97, 803 cm ; H NMR (300 MHz, DMSO-d
i
. Yield 98%,
[19] (a) Azizi, N.; Aryanasab, F.; Torkian, L.; Ziyaei-
Halimehjani, A.; Saidi, M. R. J Org Chem 2006, 71,
3634–3635; (b) Ziyaei-Halimehjani, A.; Marjani, K.;
Ashouri, A.; Green Chem 2010, 12, 1306–1310, and
the references are therein.
◦
−
1
1
9
3
(
7
6
); δ
.04 (t, J = 5.94Hz, 4H), 3.61 (s, br, 8H), 3.73
s, br, 4H), 4.04 (t, J = 6Hz, 4H), 4.14 (s, br, 4H),
[
20] Beers, W. H.; Reich, E. Nature 1970, 228, 917–
.31 (d, J = 9.2Hz, 2H), 7.37 (t, J = 6.9Hz, 2H),
.85–7.89 (m, 4H), 8.69 (d, J = 8.4Hz, 2H) ppm;
); δ 34.8, 50.5, 51.4, 65.4,
5.6, 67.1, 114.3, 116.6, 123.7, 125.1, 126.7, 128.2,
29.1, 129.6, 134.8, 155.9, 195.1 ppm; Anal. calcd
NO : C, 58.59; H, 5.21; N, 4.02. Found:
922.
13
7
C
[21] Stewart, W. E.; Siddal, T. H. Chem Rev 1970, 70,
17–551.
5
NMR (300 MHz, DMSO-d
6
[
22] Wiberg, K. B.; Rablen, P. R.; Rush, D. J.; Keith, T. A.
J Am Chem Soc 1995, 117, 4261–4270.
23] Vassilev, N. G.; Dimitrov, V. S. J Mol Struct 1999,
484, 39–47.
6
1
[
for C26
H19Cl
2
4
C, 58.44; H, 5.37; N, 4.38.
[24] Cox, C.; Lectka, T. Acc Chem Res 2000, 33, 849–
58.
25] Kang, Y. K.; Park, H. S.; J Mol Struct (Theochem)
004, 676, 171–176.
26] Holloway, C. E.; Gitlitz, M. H. Can J Chem 1967, 45,
2659–2663.
8
[
[
2
REFERENCES
[
[
[
[
[
[
[
[
[
1] Cesur, O. N.; Guner, H.; Uzun, M.; Kiraz, M.; Kaya,
D. Farmaco 1995, 50, 361–364.
2] Gunay, N. S.; Capan, G.; Ulusoy, N.; Ergenc, N.; Otuk,
G.; Kaya, D. Farmaco 1999, 54, 826–831.
[27] Gayathri
Dew,
K.
R.;
Manogaran,
S.;
Sathyanarayana, D. N. Phosphorus Sulfur Sili-
con Relat Elem 1981, 11, 47–54.
[28] Vassilev, N. G.; Dimitrov, V. S. J Mol Struct 1999,
484, 39–47.
[29] Cox, C.; Lectka, T. Acc Chem Res 2000, 33, 849–858.
[30] Kang, Y. K.; Park, H. S. J Mol Struct (Theochem)
2004, 676, 171–176.
[31] Yamagami, C. Y.; Takao, N.; Takeuchi, V. Aust J
Chem 1986, 39, 457.
[32] Cox, C.; Lectka, T. J Org Chem 1998, 63, 2426–
2427.
[33] Rablen, P. R. J Org Chem 2000, 65, 7930–7937.
[34] Basso, E. A.; Pontes, R. M. J Mol Struct (Theochem)
2002, 594, 199–206.
[35] Deetz, M. J.; Forbes, C. C.; Jonas, M.; Malerich, J. P.;
Smith, B. D.; Wiest, O. J Org Chem 2002, 67, 3949–
3952.
3] Farghaly, A. O.; Moharram, A. M. Boll Chim Farm
1
999, 138, 280–289.
4] Xu, L. Z.; Jiao, V; Zhang, S. S.; Kuang, S. P. Bull
Korean Chem Soc 2002, 23, 1699–1701.
5] Ozkirimli, S.; Apak, T. I.; Kiraz, M.; Yegenoglu, Y.
Arch Pharmacol Res 2005, 28, 1213–1218.
6] Schonenberger, V. H.; Lippert, P. Pharmazie 1972,
2
7, 139–145.
7] Capan, G; Ergenc, N.; Buyuktimkin, S.; Yulug, N. Sci
Pharm 1993, 61, 243–250.
8] Chourasia, M. R.; Tyagi, D. Indian J Phys Nat Sci
1
999, 15, 15–21.
9] Imamura, V.; Ohtake, N.; Jona, H.; Shimizu, A.;
Moriya, M.; Sato, H.; Sugimoto, Y.; Ikeura, C.; Iy-
onaga, H.; Nakano, M.; Nagano, R.; Abe, S.; Yamada,
Heteroatom Chemistry DOI 10.1002/hc