PEG-SO3H as a new, highly efficient and homogeneous polymeric catalyst for the synthesis of bis(indolyl)methanes and 4,4′-(arylmethylene)-bis(3-methyl-1-phenyl-1Hpyrazol-5-ol)s in water

Alireza Hasaninejad1, Mohsen Shekouhy1, Abdolkarim Zare2, S. M. S. Hoseini Ghattali1, Nooshin Golzar1
1Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, Iran
2Department of Chemistry, Payame Noor University (PNU), Iran

Tóm tắt

Từ khóa


Tài liệu tham khảo

A. Curzons, C.C. Constable, V.L. Cunningham, Clean Prod. Process. 1 (1999)

R. Gani, C. Jiménez-Gonzalez, A. Kate, P.A. Crafts, M. Jones, L. Powell, J.H. Atherton, J.L. Cordiner, Chem. Eng. 1 (2006) 30

A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi-Zare, M.H. Beyzavi, F. Khedri, F. Asadi, N. Hayati, A. Asifi, J. Iran. Chem. Soc. 7 (2010) 461

A. Shaabani, R. Ghadari, A. Rahmati, A.H. Rezayan, J. Iran. Chem. Soc. 6 (2009) 710

R.S. Bhosale, S.R. Sarda, R.P. Giram, D.S. Raut, S.P. Parwe, S.S. Ardhapure, R.P. Pawar, J. Iran. Chem. Soc. 6 (2009) 519.

C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997.

Organic Synthesis in Water, P.A. Grieco (Ed.), Blackie Academic and Professional, London, 1998

U.M. Lindstrom, Chem. Rev. 102 (2002) 2751

S. Kobayashi, K. Manabe, Acc. Chem. Res. 35 (2002) 209

S. Narayan, J. Muldoon, M.G. Fin, V.V. Folkin, H.C. Kolb, K.B. Sharpless, Angew. Chem., Int. Ed. 44 (2005) 3275

C.-J. Li, Chem. Rev. 93 (1993) 2023

N. Azizi, E. Akbari, M.R. Saidi, J. Iran. Chem. Soc. 6 (2009) 165

N. Azizi, A. Khajeh Amiri, M. Bolourtchian, M.R. Saidi, J. Iran. Chem. Soc. 6 (2009) 749

M.M. Heravi, A. Ghods, F. Derikvanda, K. Bakhtiari, F.F. Bamoharram, J. Iran. Chem. Soc. 6 (2009) 615

H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 6 (2009) 890

A. Hasaninejad, A. Zare, M.R. Mohammadizadeh, Z. Karami, J. Iran. Chem. Soc. 6 (2009) 153.

S. Ribe, P. Wipf, Chem. Commun. (2001) 299.

S.-J. Tu, J.-F. Zhou, Z.-S. Lu, X. Deng, D.-Q. Shi, S.-H. Wang, Synth. Commun. 32 (2002) 3063.

J. Eames, M. Watkinson, J. Org. Chem. (2001) 1213.

C.C. Tzschucke, C. Markert, W. Bannwarth, S. Roller, A. Hebel, R. Haag, Angew. Chem. 114 (2002) 4136.

L. Wang, J. Han, H. Tian, J. Sheng, Z. Fan, X. Tang, Synlett (2005) 37.

X. Wang, Z. Quan, F. Wang, M. Wang, Z. Zhang, Z. Li, Synth. Commun. 36 (2006) 451.

A.R. Kiasat, M.F. Mehrjardi, Catal. Commun. 9 (2008) 1497.

J.K. Porter, C.W. Bacon, J.D. Robbins, D.S. Himmelsbach, H.C. Higman, J. Agric. Food Chem. 25 (1977) 88

T. Osawa, M. Namiki, Tetrahedron Lett. 24 (1983) 4719

G. Bifulco, I. Bruno, R. Riccio, J. Lavayre, G. Bourdy, J. Nat. Prod. 57 (1994) 1254

R. Bell, S. Carmeli, N. Sar, J. Nat. Prod. 57 (1994) 1587

T.R. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa, H. Yukawa, J. Nat. Prod. 63 (2000) 596

M.A. Zeligs, J. Med. Food, 1 (1998) 67

C. Grubbs, V. Steele, T. Casebolt, M.M. Juliana, I. Eto, L.M. Whitaker, Anticancer Res. 15 (1995) 709

S.H. Benabadji, R. Wen, J. Zheng, X. Dong, S. Yuan, Acta Pharmacol. Sin. 25 (2004) 666

M.J. Anderton, M.M. Manson, R. Verschoyle, A. Gescher, W.P. Steward, M.L. Williams, D.E. Mager, Drug Metab. Dispos. 32 (2004) 632.

M. Shiri, M.A. Zolfigol, H.G. Kruger, Z. Tanbakouchian, Chem. Rev. 110 (2010) 2250

G.W. Gribble, J. Chem. Soc., Perkin Trans. 1 (2000) 1045

R.J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970

R.J. Sundberg, Indoles, Academic Press, San Diego, CA, 1996

J.A. Joule, Science of Synthesis (indoles), E.J. Thomas (Ed.), Georg Thieme Verlag, Stuttgart, New York, 2000, Vol. 10, pp. 361–652.

M. Chakrabarty, R. Basak, Y. Harigaya, Heterocycles 55 (2001) 2431.

B.P. Bandgar, K.A. Shaikh, Tetrahedron Lett. 44 (2003) 1959.

H. Koshima, W. Matsuaka, J. Heterocycl. Chem. 39 (2002) 1089.

A. Hasaninejad, A. Parhami, A. Zare, A. Khalafi- Nezhad, A. Nasrolahi Shirazi, A.R. Moosavi Zare, Polish J. Chem. 82 (2008) 565.

A. Hasaninejad, A. Zare, H. Sharghi, M. Shekouhy, R. Khalifeh, A. Salimi Beni, A.R. Moosavi Zare, Can. J. Chem. 85 (2007) 416.

A. Hasaninejad, A. Zare, H. Sharghi, K. Niknam, M. Shekouhy, ARKIVOC xiv (2007) 39.

A. Khalafi-Nezhad, A. Parhami, A. Zare, A.R. Moosavi Zare, A. Hasaninejad, F. Panahi, Synthesis (2008) 617.

A. Zare, A. Parhami, A.R. Moosavi-Zare, A. Hasaninejad, A. Khalafi-Nezhad, M.H. Beyzavi, Can. J. Chem. 87 (2009) 416

J.S. Yadav, B.V.S. Reddy, S. Sunitha, Adv. Synth. Catal. 45 (2003) 349

D.G. Gu, S.J. Ji, Z.Q. Jiang, M.F. Zhou, T.P. Loh, Synlett (2005) 959.

J.S. Yadav, B.V.S. Reddy, C.V.S.R. Murthy, G.M. Kumar, C. Madan, Synthesis (2001) 783

H. Firouzabadi, N. Iranpour, M. Jafarpour, A. Ghaderi, J. Mol. Cat. A: Chem. 253 (2006) 249

J.S. Yadav, B.V.S. Reddy, G. Satheesh, A. Prabhakar, A.C. Kunwar, Tetrahedron Lett. 44 (2003) 2221

G. Babu, N. Sridhar, P.T. Perumal, Synth. Commun. 30 (2000) 1609

D.P. Chen, L.B. Yu, P.G. Wang, Tetrahedron Lett. 37 (1996) 4467

R. Nagarajan, P.T. Perumal, Tetrahedron 58 (2000) 1229

X.L. Mi, S.Z. Luo, J.Q. He, J.P. Chen, Tetrahedron Lett. 5 (2004) 4567

L. Wang, J. Han, H. Tian, J. Sheng, Z. Fan, X. Tang, Synlett (2005) 37.

S. Kobayashi, M. Araki, M. Yasuda, Tetrahedron Lett. 6 (1995) 5773.

J. Elguero, A.R. Katritzky, C.W. Rees (Eds.), Comprehensive Heterocyclic Chemistry: Pyrazoles and their Benzo Derivatives, Vol. 5, Pergamon Press, Oxford, 1984

H. Nakagawa, R. Ohyama, A. Kimata, T. Suzuki, N. Miyata, Bioorg. Med. Chem. Lett. 16 (2006) 5939

C. Coimra, F. Boris-Möller, M. Drqke, T. Wieloch, Acta Neuropathology 92 (1996) 447.

T. Kessler, T. Aybek, G. Neidhart, S. Dogan, D. Bremerich, D. Lischke, C. Byhahan, J. Cardiothoracic and Vascular Anesthesia 19 (2005) 32.

S. Sugiura, S. Ohno, O. Ohtani, K. Izumi, T. Kitamikado, H. Asai, K. Kato, J. Med. Chem. 20 (1977) 80.

L.C. Behr, R. Fusco C.H., Jarboe, The Chemistry of Heterocyclic Compounds, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, A. Weissberger (Ed.), Interscience Publishers, New York, 1967.

C.E. Rosiere, M.I. Grossman, Science 113 (1951) 651.

D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28 (1985) 256.

R.N. Mahajan, F.H. Havaldar, P.S. Fernandes, J. Ind. Chem. Soc. 68 (1991) 245.

P.M.S. Chauhan, S. Singh, R.K. Chatterjee, Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 32 (1993) 858.

D. Singh, D. Singh, J. Ind. Chem. Soc. 68 (1991) 165.

M. Londershausen, Pestic. Sci. 48 (1996) 269.

The Chemistry of Synthetic Dyes and Pigments, H.A. Lubs (Ed.), American Chemical Society, Washington D.C., 1970.

A.B. Uzoukwu, Polyhedron 12 (1993) 2719

R.C. Maurya, R. Verma, Ind. J. Chem., Sect. A 36 (1997) 596

A.D. Garnovskii, A.I. Uraev, V.I. Minkin, ARKIVOC iii (2004) 29.

D. Singh, D. Singh, J. Chem. Eng. Data 29 (1984) 355.

B.I. Buzykin, T.I. Lonshchakova, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) (1971) 2224.

W. Wang, S.-X. Wang, X.-Y. Qin, J.-T. Li, Synth. Commun. 35 (2005) 1263.

M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Synthesis (2008) 1933.

X. Zeng, S. Ji, S. Wang, Tetrahedron 61 (2005) 10235.

M.L. Deb, P.J. Bhuyan, Tetrahedron Lett. 47 (2006) 1441.

J.-B. Meng, D.-M. Du, W.-G. Wang, Y.-M. Wang, Chem. J. Chin. Univ. 15 (1994) 528.

M.A. Zolfigol, P. Salehi, M. Shiri, Z. Tanbakouchian, Catal. Commun. 8 (2007) 173.

K. Tabatabaeian, M. Mamaghani, N. Mahmoodi, A. Khorshidi, Can. J. Chem. 84 (2006) 1541.

K. Sujatha, G. Shanthi, N.P. Selvam, S. Manoharan, P.T. Perumal, M. Rajendran, Bioorg. Med. Chem. Lett. 19 (2009) 4501.

M. Shiri, M.A. Zolfigol, Tetrahedron 65 (2009) 587.

K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3 (2006) 318

R. Nagarajan, P.T. Perumal, Synth. Commun. 32 (2002) 105

C.J. Magesh, R. Nagarajan, M. Karthik, P.T. Perumal, Appli. Catal. A: Gen. 266 (2004) 1

L. Wang, J.H. Han, T. Sheng, J.Z. Fan, X. Tang, Synlett (2005) 337

H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Mol. Catal. A: Chem. 244 (2006) 168

J.S. Yadav, B.V.S. Reddy, P. Sreedhar, R.S. Rao, K. Nagaiah, Synthesis (2004) 2381

A. Shaabani, E. Soleimani, Z. Badri, Synth. Commun. 37 (2007) 629

B. Staskun, J. Org. Chem. 29 (1964) 1153.