Green and diastereoselective synthesis of trans-3-(5-methylisoxazol-3-yl)-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazines

محورهای موضوعی : Iranian Journal of Catalysis

Mehdi Shafiee ¹ (Chemistry Department, Malek-ashtar University of Technology, Shahin-shahr, 83145-115, Iran.)
Ahmad Reza Khosropour ² (Catalysis Division, Department of Chemistry, Faculty of Science, University of Isfahan, Isfahan 81746-7344, Iran.)
Iraj Mohammadpoor-Baltork ³ (Catalysis Division, Department of Chemistry, Faculty of Science, University of Isfahan, Isfahan 81746-7344, Iran.)
Majid Moghadam ⁴ (Catalysis Division, Department of Chemistry, Faculty of Science, University of Isfahan, Isfahan 81746-7344, Iran.)
Shahram Tangestaninejad ⁵ (Catalysis Division, Department of Chemistry, Faculty of Science, University of Isfahan, Isfahan 81746-7344, Iran.)
Valiollah Mirkhani ⁶ (Catalysis Division, Department of Chemistry, Faculty of Science, University of Isfahan, Isfahan 81746-7344, Iran.)
Hamid Reza Khavasi ⁷ (Department of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran.)

تاریخ دریافت : 1392/08/12 تاریخ پذیرش : 1392/11/14 تاریخ انتشار : 1393/06/10

کلید واژه: green chemistry, Betti base, Aryl aldehydes, Dihydro-2H-naphtho[2, 3-e][1, 3]oxazines, p-TSA,

چکیده مقاله :

Reaction between aromatic aldehydes and 3–methyl-1-phenyl-2-pyrazoline-5-one catalyzed by nano-SiO2/HClO4 in water under reflux provided a simple and efficient route for the synthesis of 4-((5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(aryl)methyl)-3-methyl-1-phenyl-1H-pyrazol-5-ol derivatives in high yields.

منابع و مأخذ:

[1] (a) W.M. Duffin, I. M. Rollo, Br. J. Pharmacol. 12 (1957) 171-175. (b) M. E. Kuehne, E. A. Konopke, J. Med. Chem. 5 (1962) 257-263. (c) J. B. Chylinska, T. Urbanski, J. Med. Chem. 6 (1963) 484-491. (d) J. B. Chylinska, M. Janowiec, T. Urbanski, Br. J. Pharmacol.43 (1971) 649-657. (e) N. Latif, N. Mishriky, F. M. Massad, Aust. J. Chem. 35 (1982) 1037-1043. (f) L.-Y. Hsu, C.-H. Lin, Heterocycles 43 (1996) 2687-2699. (g) O. S. Pedersen, E. B. Pedersen, Synthesis (2000) 479-495. (h) A.J. Cocuzza, D. R. Chidester, B. C. Cordova, S. Jeffrey, R. L. Parsons, L. T. Bacheler, S. Erickson-Viitanen, G. L. Trainor, S. S. Ko, Bioorg. Med. Chem. Lett. 11 (2001) 1177-1179. (i) I. Kmentova, H. S. Sutherland, B.D. Palmer, A. Blaser, S. G. Franzblau, B. J. Wan, ; Y. H. Wang, Z. K. Ma, W.A. Denny, A. M. Thompson, J. Med. Chem. 53 (2010) 8421-8439.( j) A. M. Thompson, H. S. Sutherland, B. D. Palmer, I. Kmentova, A. Blaser, S. G. Franzblau, B. J. Wan, Y. H. Wang, Z.K. Ma, W.A. Denny, J. Med. Chem. 54 (2011) 6563-6585. (k) R. Sawant, L. Bhangale, J. Wadekar, P. Gaikwad, Farmacia 60 (2012) 32-39.

[2] (a) A. Douhi, A. Fradet, Polym. Bull. 36 (1996) 455-462. (b) K. C. Chen, H. T. Li, W. B. Chen, C. H. Liao, K. W. Sun, F. C. Chang, Polym. Int. 60 (2011) 436-442.
[3] (a) M. Tomasulo, S. Sortino, A. J. P. White, F. M. Raymo, J. Org. Chem. 70 (2005) 8180-8189. (b) E. Deniz, S. Ray, M. Tomasulo, S. Impellizzeri, S. Sortino, F. M. Raymo, J. Phys. Chem. A 114 (2010) 11567-11575. (c) Y. Prostota, P.J. Coelho, J. Pina, J.S. de Melo, Photochem. Photobiol. Sci.10 (2011) 1346-1354.
[4] M. Tomasulo, F. M.Raymo, Org. Lett. 7 (2005) 4633-4636.
[5] (a) H.B. Zhou,  J. H. Lee, C. G. Mayne, K. E. Carlson, J.A. Katzenellenbogen, J. Med. Chem. 53 (2010) 3349-3360. (b) H. Yang, N. Goyal, J.R. Ella-Menye, K. Williams, G.J. Wang, Synthesis 44 (2012) 561-568.
[6] H. Van de Poel, G. Guillaumet, M. C. Viaud-Massuard, Tetrahedron Lett. 43 (2002) 1205-1208.
[7] S.K. Das, C. Abbineni, K.V.L.N. Rao, J. Iqbal, R.K. Babu,  R. Chakrabarti, Lett. Drug Des. Discov. 4 (2007) 27-32.
[8] D. Briel, A. Rybak, C. Kronbach, K. Unverferth, C. M. G. Tanarro, M. Gutschow, J. Heterocycl. Chem. 47 (2010) 634-639.
[9] P. Zhang, E. A. Terefenko, A. Fensome, Z. Zhang, Y. Zhu, J. Cohen, R. Winneker, J. Wrobel, J. Yardley, Bioorg. Med. Chem. Lett. 12 (2002) 787.
[10] E. Rajanarendar, G. Mohn, A. S. R. Reddy, Indian J. Chem. (47B) 2008 112-116.
[11] M. K. Gupta, A. M. Tyagi, D. Singh, A. Kumar, Med. Chem. Res. 19 (2010) S82-S82.
[12] (a) M. Tomasulo, S. Sortino, F. M. Raymo, Org. Lett. 7 (2005) 1109–1112; b) Y. Prostota, P. J. Coelho, J. Pina, J.S. de Melo, Photochem. Photobiol. Sci. 10 (2011) 1346-1354.
[13] (a) B. P. Mathew, A. Kumar, S. Sharma, P. K. Shukla, M. Nath, Eur. J. Med. Chem. 45 (2010) 1502-1507. (b) A. N. Mayekar, H. S. Yathirajan, B. Narayana, B. K. Sarojini, N. S. Kumari, W. T. A Harrison, Int. J. Chem. 3 (2011) 74-86. (c) D. Shi, S. Rong, G. Dou, M. Wang, J. Comb. Chem. 12 (2010) 25–30.
[14] (a) X.X. Zhang, J. S. Bradshaw, R. M. Izatt, Chem. Rev. 97 (1997) 3313-3362. (b) W. Wang, F. Ma, X. Shen, C. Zhang, Tetrahedron: Asymmetry 18 (2007) 832-837. (c) D. Pitt, E. Gonzales, A. H. Cross, M.P. Goldberg, Brain Res. 1309 (2010) 146-154. (d) S. Maeng, C.A. Zarate, J. Du, R.J. Schloesser, J. McCammon, G. Chen, H. K. Manji, Biol. Psychiatry 63 (2008) 349-352. (e) P. A. Bradley, R. J. Carroll, Y. C. Lecouturier, R. Moore, P. Noeureuil, B. Patel, J. Snow, S. Wheeler, Org. Process. Res. Dev. 14 (2010) 1326-1336. (f) M. Badland, M. P. Burns, R. J. Carroll, R. M. Howard, D. Laity, N. J. Wymer, Green Chem. 13 (2011) 2888-2894.
[15] C. Cardellicchio, M. A. M. Capozzi, F. Naso, Tetrahedron: Asymmetry 21 (2010) 507-517.
[16] A. Y. Shen, C. T. Tsai, C. L. Chen; Eur. J. Med. Chem. 34 (1999) 877-882.
[17] (a) C. Cimarelli, A. Mazzanti, G. Palmieri, E. Volpini, J. Org. Chem. 66 (2001) 4759-4765. (b) C. Cimarelli, G. Palmieri, E. Volpini, Tetrahedron: Asymmetry 13 (2002) 2417-2426. (c) C. Cimarelli, G. Palmieri, E. Volpini, J. Org. Chem. 68 (2003) 1200-1206.
[18] J. Feng, S. Dastgir, C.-J. Li, Tetrahedron Lett. 49 (2008) 668-671.
[19] (a) M. Rostami,; A.R. Khosropour, V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam, S Tangestaninejad, Synlett (2011) 1677-1682. (b) M. Rostami, A.R. Khosropour, V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, Monatsh. Chem. 142 (2011) 1175-1180. (c) M. Rostami, A.R. Khosropour, V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, Appl. Catal. A: Gen. 397 (2011) 27-34.
[20] M. Shafiee, A. R. Khosropour, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad,; V. Mirkhani, Tetrahedron Lett. 53 (2012) 3086-3090.
[21] Dunning, J. T. H. J. Chem. Phys. 1989, 90, 1007-1023.
[22] Turbomole V6.3, a development of the University of Karlsruhe and Forschungazentrum Karlsruhe GmbH, 1989-2007, Turbomole, GmbH, since 2007; available from http://www.turbomole.com.