An effective and mild oxidative aromatization of isoxazolines and 2-pyrazolines by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxalane promoted by ammonium iodide in water/MeCN
Subject Areas : Iranian Journal of Catalysis
Akbar Mobinikhaledi
1
,
Kaveh Khosravi
2
,
Samira Kazemi
3
1 - Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
2 - Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
3 - Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
Keywords:
Abstract :
[1] T.L. Gilchrist, (1998) in Heterocyclic Chemistry, 3rd ed.; Addison Wesley Longman: Edinburgh Gate, 1997.
[2] D. Lednicer, (1998) Strategies for Organic Drugs Synthesis and Design, Wiley & Sons, New York.
[3] Y. Li, H.Q. Zhang, J. Liu, X.P. Yang, Z. J. Liu, J. Agric. Food. Chem. 54 (2006) 3636-3640.
[4] M.A. Raslan, R.M. Abd El-Aal, M.E. Hassan, N.A. Ahmed, K.U. Sadek, J. Chin. Chem. Soc. 48 (2001) 91-99.
[5] G.M. Garvin, J.L. Jackson, J.M. McQuiston, M.J. Ricks, T.D. Thibault, J.A. Turner, J.C. VanHeertum, M.R. Weimer, Pest. Manage. Sci. 58 (2002) 1175-1186.
[6] N. Nakamichi, Y. Kawashita, M. Hayashi, Org. Lett. 4 (2002) 3955-3957.
[7] N. Nakamichi, Y. Kawashita, M. Hayashi, Synthesis (2004) 1015-120.
[8] M. Hayashi, Y. Kawashita, Lett. Org. Chem. 3 (2006) 571-578.
[9] Y. Kawashita, C. Ueba, M. Hayashi, Tetrahedron. Lett. 47 (2006) 4231-4233.
[10] Y. Kawashita, N. Nakamichi, H. Kawabata, M. Hayashi, Org. Lett. 5 (2003) 3713-3715.
[11] J.N. Shah, C.K. Shah, J. Org. Chem. 43 (1978) 1266-1267.
[12] W.A.F. Goldstone, R.O.C. Norman, J. Chem. Soc. Chem. Commun. (1966) 1537-1538.
[13] K. Auwers, P. Heimke, Liebigs. Ann. 458 (1927) 186-187.
[14] L.I. Smith, K.L. Howard, J. Am. Chem. Soc. 65 (1943) 156-159.
[15] N.K. Kochetkov, S.D. Sokolov, in Advances in Heterocyclic Chemistry, Academic Press, New York, 1965, p. 420.
[16] R.P. Dodwadmath, T.S. Wheeler, Proc. Ind. Acad. Sci. 2A (1935) 438-451.
[17] S.P. Singh, D. Kumar, O. Prakash, R.P. Kapoor, Synth. Commun. 27 (1997) 2683-2689.
[18] G.S. Abitha, G.S.K. Kumar Reddy, Ch.S. Reddy,
N. Fatima, J. S. Yadav, Synthesis (2003) 1267-1270.
[19] C.J. Easton, G.A. Heath, C. Merricc, M. Hughes,
J. Chem. Soc. Perkin Trans. 1 (2001) 1168-1174.
[20] A.H. Blatt, J. Am. Chem. Soc. 71 (1949) 1856-1861.
[21] D. Simoni, M. Robert, F.P. Invidiata, R. Rondanin,
C. Malagutti, A. Mazzali, M. Ross, S. Grimaudo,
F. Capone, L. Dusoncher, J. Med. Chem. 44 (2001) 2308-2318.
[22] C.P. Chuang, M.C. Jiang, Tetrahedron 45 (1999) 11229-11236.
[23] R.K. Chang, K. Kim, Tetrahedron. Lett. 41 (2000) 8499-8503.
[24] M. Schnürch, R. Flasik, A.F. Khan, M. Spina, M.D. Mihovilovic, P. Stanetty, Eur. J. Org. Chem. (2006) 3283-3307.
[25] L. Bianchi, C. Dellerba, F. Grasparrini, M. Novi, C. Tavani, Arkivoc xi (2002) 142-158.
[26] (a) B. Das, B. Veeranjaneyulu, M. Krishnaiah, J. Mol. Catal. A: Chem. 284 (2008) 116-119. (b) A. Bunge, H.J. Hamann, J. Liebscher, Tetrahedron. Lett. 50 (2009) 524-526. (c) A. Bunge, H.J. Hamann, E. McCalmont, J. Liebscher, Tetrahedron Lett. 50 (2009) 4629-4632. (d) B. Das, M. Krishnaiah, B. Veeranjaneyulu, B. Ravikanth, Tetrahedron Lett. 48 (2007) 6286-6289. (e) K. Zmitek, M. Zupan, S. Stavber, J. Iskra, J. Org. Chem. 72 (2007) 6534-6540 (f) K. Zmitek, M. Zupan, S. Stavber, J. Iskra, Org. Lett. 8 (2006) 2491-2494. (g) Y. Li, H.D. Hao, Q. Zhang, Y. Wu, Org. Lett. 11 (2009) 1615-1618. (h) P. Ghorai, P.H. Dussault, Org. Lett. 10 (2008) 4577-4579.
[27] (a) K. khosravi, A. Mobinikhaledi, S. Kazemi,
D. Azarifar, P. Rahmani, Iran. J. Catal. 4 (2014) 25-31. (b) D. Azarifar, Z. Najminejad, K. Khosravi, J. Iran. Chem. Soc. 10 (2013) 979-983. (c) D. Azarifar,
Z. Najminejad, K. Khosravi, Synth. Commun. 43 (2013) 826-836. (d) D. Azarifar, K. Khosravi, J. Iran. Chem. Soc. 8 (2011) 1006-1013. (e) D. Azarifar, K. Khosravi, Z. Najminejad, K. Soleimani, J. Iran. Chem. Soc.
9 (2012) 321-326. (f) D. Azarifar, K. Khosravi, Synlett (2010) 2755-2758. (g) D. Azarifar, K. Khosravi,
F. Soleimanei, Synthesis (2009) 2553-2556.
[28] L. Chai, Y. Zhao, Q. Sheng, Z.Q. Liu, Tetrahedron Lett. 47 (2006) 9283-9285.
[29] M.A. Zolfigol, D. Azarifar, S. Mallakpour, I. Mohammadpoor-Baltork, A. Forghaniha, B. Maleki, M. Abdollahi-Alibeik, Tetrahedron Lett. 47 (2006) 833-836.
[30] B. Han, Zh. Liu, Q. Liu, L. Yang, Z.L. Liu, W. Yu, Tetrahedron 62 (2006) 2492-2496.
[31] R. Ghorbani-Vaghei, D. Azarifar, B. Maleki, Bull. Korean. Chem. Soc. 25 (2004) 953-954.
[32] D. Azarifar, M.A. Zolfigol, B. Maleki, Bull. Korean. Chem. Soc. 25 (2004) 23-24.
[33] D. Azarifar, B. Maleki, M. Setayeshnazar, Heterocycles 75 (2008) 669-6675.
[34] H. Adibi, A.R. Hajipour, H. Jafari, Chem. Heterocycl. Compd. 44 (2008) 802-806.
[35] R. Ghorbani-Vaghei, D. Azarifar, A. Khazaei, B. Maleki, Phosphorus, Sulfur Silicon Relat. Elem. 179 (2004) 1877-1881.
[36] D. Azarifar, E. Nadimi, M. M. Ghanbari, Chin. Chem. Lett. 22 (2011) 447-450.
[37] G. Su, W.T. Wu, J.T. Wang, L.M. Wu, Chin. Chem. Lett. 19 (2008) 1013-1016.
[38] M.A. Zolfigol, D. Azarifar, B. Maleki, Tetrahedron Lett. 45 (2004) 2181-2183.
[39] G.S. Abitha, G.S.K. Kumar Reddy, C.S. Reddy, N. Fatima, J.S. Yadav, Synthesis (2003) 1267-1270.
[40] S. Ponnala, D.P. Sahu, Synth. Commun. 36 (2006) 2189-2194.
[41] M.M. Heravi, R. Hekmat-Shoar, L. Pedram, J. Mol. Catal. A: Chem. 231 (2005) 89-91.
[42] D. Azarifar, A. Gharshasebi, Heterocycles 68 (2006) 1209-1215.
[43] D. Azarifar, B. Maleki, K. Mohammadi, Heterocycles 71 (2007) 683-689.
[44] (a) D. Azarifar, M. Shaebanzadeh, Molecules 7 (2002) 885-895. (b) L.D. Nunno, A. Scilimati, P. Vitale, Tetrahedron 58 (2002) 2659-2665. (c) R.M. Kedar, N.N. Vidhale, Orient. J. Chem. (1997) 143-148. (d) A.H. Blatt, J. Am. Chem. Soc. 71 (1949) 1861-1862.
