J IRAN CHEM SOC
To compare the applicability and efficiency of our cata-
lyst with catalysts reported for the synthesis of 1-(benzo-
thiazolylamino) methyl-2-naphthol 4e, we have tabulated
the results for these catalysts (Table 3). It is apparent from
Table 3 that oxalic acid remarkably improved the synthesis
of 1-(benzothiazolylamino) methyl-2-naphthol 4e, in terms
of reaction time and yield.
14. D.F. Shi, T.D. Bradshaw, S. Wrigley, C.J. McCall, P. Lelieveld, I.
Fichtner, M.F.G. Stevens, J. Med. Chem. 39, 3375 (1996)
1
5. G. Wells, T.D. Bradshaw, P. Diana, A. Seaton, D.F. Shi, A.D.
Westwell, M.F.G. Stevens, Bio. Org. Med. Chem. Lett. 10, 513
(2000)
16. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Brad-
shaw, A.D. Westwell, M.F.G. Stevens, J. Med. Chem. 44, 1446
(
2001)
1
7. R.S. Chopade, R.H. Bahekar, P.B. Khedekar, K.P. Bhusari, A.R.
Rao, Arch. Pharm. 335, 381 (2002)
1
1
8. N.D. Amnerkar, K.P. Bhusari, Eur. J. Med. Chem. 45, 149 (2010)
9. M. Palkar, M. Noolvi, R. Sankangoud, V. Maddi, A. Gadad,
L.V.G. Nargund, Arch. Pharm. 343, 353 (2010)
Conclusion
2
0. T. Singh, V.K. Srivastava, K.K. Saxena, S.L. Goel, A. Kumar,
We have developed a new, general and efficient proce-
dure for the one-pot synthesis of 1-(benzothiazolylamino)
methyl-2-naphthol by coupling various aromatic aldehydes,
Arch. Pharm. 339, 466 (2006)
21. S.J. Choi, H.J. Park, S.K. Lee, S.W. Kim, G. Han, H.Y.P. Choo,
Bio. Org. Med. Chem. 14, 1229 (2006)
2. C.J. Paget, K. Kisner, R.L. Stone, D.C. Delong, J. Med. Chem.
2
2-naphthol and 2-aminobenzothiazole using oxalic acid
1
2, 1016 (1969)
as a reaction mediator under solvent-free conditions. This
protocol has the advantages of shorter reaction times, low
costs, solvent-free condition, easy work-up, excellent yields,
elimination of solvents, environmentally friendly and lack
of need for column chromatography, and it follows the prin-
ciples of green chemistry. Also the use of oxalic acid has
some special merits such as being highly efficient, low cost,
non-toxic, environmentally friendly and readily available
reagent which can be conveniently handled and removed
from the reaction mixture. We believe that this procedure
is convenient, economical and eco-friendly process for the
synthesis of 1-(benzothiazolylamino) methyl-2-naphthol
which has many biological and medicinal applications.
23. R.C. Young, R.C. Mitchell, T.H. Brown, C.R. Ganellin, R. Grif-
fiths, M. Jones, K.K. Rana, D. Saunders, I.R. Smith, N.E. Sore,
T.J. Wilks, J. Med. Chem. 31, 656 (1988)
2
4. F. Pirrone, V. Hydroxyquinolines, Gazz. Chim. Ital. 70, 520
1940)
(
25. J.P. Phillips, E.M. Barrall, J. Org. Chem. 21, 692 (1956)
26. J.P. Phillips, Chem. Rev. 56, 271 (1956)
2
2
7. J.B. Littman, W.R. Brode, J. Am. Chem. Soc. 52, 1655 (1930)
8. Y. Wang, X. Li, K. Ding, Tetrahedron Asymmetry 13, 1291
(
2002)
29. C. Cardellicchio, G. Ciccarella, F. Naso, F. Perna, P. Tortorella,
Tetrahedron 55, 14685 (1999)
3
3
3
0. I. Szatmari, A. Tamas, L. Martinek, F. Fulop, Tetrahedron 59,
877 (2003)
1. I. Szatmari, A. Heteny, L. Lazar, F. Fulop, J. Heterocycl. Chem.
2
41, 367 (2004)
2. M. Heydenreich, A. Koch, S. Klod, I. Szatmari, F. Fulop, E.
Kleinpeter, Tetrahedron 62, 11081 (2006)
Acknowledgments We gratefully acknowledge financial sup-
port from the Research Council of the University of Sistan and
Baluchestan.
33. N. Gyemant, H. Engi, Z. Schelz, I. Szatmari, D. Toth, F. Fulop, J.
Molnar, P. Witte, Br. J. Cancer 103, 178 (2010)
3
4. A. Ohanian, S. Javanshir, M.M. Heravi, F.F. Bamoharram, 13th
International Electronic Conference on Synthetic Organic Chem-
istry (ECSOC-13) November 2009
References
35. A. Kumar, M.S. Rao, V.K. Rao, Aust. J. Chem. 63, 1538 (2010)
3
6. A. Shaabani, A. Rahmati, E. Farhangi, Tetrahedron Lett. 48,
1
2
.
.
C.O. Kappe, Curr. Opin. Chem. Biol. 6, 314 (2002)
V. Nair, C. Rajesh, A. Vinod, U.S. Bindu, A.R. Streekenth, S.
Mathen, L. Balagopal, Acc. Chem. Res. 36, 899 (2003)
D.J. Ramon, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)
A.A. Domling, Chem. Rev. 106, 17 (2006)
A. Domling, I. Ugi, Angew. Chem. 112, 3300 (2000)
L.F. Tietze, A. Modi, Med. Res. Rev. 20, 304 (2000)
J. Zhu, Eur. J. Org. Chem. 2003, 1133 (2003)
7291 (2007)
37. Y. Yi, G. Hongyunv, Chin. J. Org. Chem. 31, 96 (2011)
38. H.R. Shaterian, A. Hosseinian, Res. Chem. Intermed. 41, 793
(2015)
39. P.K. Sahu, P.K. Sahu, D.D. Agarwa, RSC Adv. 40, 40414 (2014)
40. P.I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 40, 3726 (2001)
41. B. List, Tetrahedron 58, 5573 (2002)
3
4
5
6
7
8
.
.
.
.
.
.
42. M.P. Brochu, S.P. Brown, D.W.C. MacMillan, J. Am. Chem.
L. Laine, A.J. Kivitz, A.E. Bello, A.Y. Grahn, M.H. Schiff, A.S.
Soc. 126, 4108 (2004)
Taha, Am. J. Gastroenterol. 107, 379 (2012)
C. DeBattista, H.B. Solvason, J.A. Breen, A.F. Schatzberg, J.
Clin. Psychopharmacol. 20, 274 (2000)
43. N. Halland, A. Braunton, S. Bachmann, M. Marigo, K.A. Jor-
gensen, J. Am. Chem. Soc. 126, 4790 (2004)
44. N. Mase, F. Tanaka, C.F. Barbas, Angew. Chem. Int. Ed. 43,
2420 (2004)
9
.
1
1
1
0. J. Das, P. Chen, D. Norris, R. Padmanabha, J. Med. Chem. 49,
819 (2006)
6
45. N.T. McDougal, W.L. Trevellini, S.A. Rodgen, L.T. Kliman, S.E.
1. R.S. Obach, A.S. Kalgutkar, T.F. Ryder, G.S. Walker, Chem. Res.
Toxicol. 21, 1890 (2008)
2. C. Borelli, M. Schaller, M. Niewerth, K. Nocker, B. Baasner, D.
Berg, R. Tiemann, K. Tietjen, B. Fugmann, S. Lang-Fugmann,
H.C. Korting, Chemotherapy 54, 245 (2008)
Schaus, Adv. Synth. Catal. 346, 346 (2004)
46. M. Caliskan, Turk. J. Zool. 24, 103 (2000)
47. M.R. Mousavi, J. Aboonajmi, M.T. Maghsoodlou, N. Hazeri, J.
Chem. Res. 38, 76 (2014)
48. N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J.
Aboonajmi, M. Lashkari, S.S. Sajadikhah, Res. Chem. Intermed.
40, 1781 (2014)
1
3. A.N. El-Shorbagi, S.I. Sakai, M.A. El-Gendy, N. Omar, H.H.
Farag, Chem. Pharm. Bull. 37, 2971 (1989)
1
3