Services on Demand
Journal
Article
Indicators
Related links
- Cited by Google
- Similars in Google
Share
South African Journal of Chemistry
On-line version ISSN 1996-840XPrint version ISSN 0379-4350
S.Afr.j.chem. (Online) vol.63 Durban 2010
RESEARCH ARTICLE
Alum-promoted synthesis of 1,8-dioxo-octahydroxanthenes in water
Balaji R. MadjeI, *; Milind B. UbaleI; Jagdish V. BharadI; Murlidhar S. ShingareII
IDepartment of Chemistry, Vasantrao Naik Mahavidyalaya, Aurangabad 431 003, M.S., India
IIDepartment of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431 004, M.S., India
ABSTRACT
A new and efficient method to synthesize a 3,3,6,6,9-aryl-1,8-dioxo-octahydroxanthene derivative using alum as catalyst was performed in aqueous media. This method has several advantages such as environmental friendliness, high yields and simple workup procedure.
Keywords: Alum, aqueous media, 3,3,6,6,9-aryl-1,8-dioxo-octahydroxanthene, condensation reaction
Full text available only in PDF format.
Acknowledgements
The authors thank the University Grants Commission (WRO), Pune, for financial support of the present work.
References
1 J.R. Dimmock, S.K. Raghavana and G.E. Bigam, Eur. J. Med. Chem., 1988, 23, 111-117. [ Links ]
2 S. Chatterjee, M. Iqbal, J.C. Kauer, J.P. Mallamo, S. Senadhi and S. Mallya, Bioorg. Med. Chem. Lett., 1996, 6, 1619-1622. [ Links ]
3 (a) D.F. Eaton, Adv. Photochem., 1986, 13, 427-487; [ Links ] (b) M. Wainwright, Biotech. Histochem., 2003, 78, 147-155. [ Links ]
4 G. Pohlers and J.C. Scaiano, Chem. Mater., 1997, 9, 3222-3230. [ Links ]
5 C.G. Knight and T. Stephens, Biochem. J., 1989, 258, 683-687. [ Links ]
6 Y.M. Shchekotikhin and T.G. Nikolaeva, Chem. Heterocycl. Comp., 2006, 42, 28-33. [ Links ]
7 F. Darviche, S. Balalaie, F. Chadegani and P. Salehi, Synth. Commun., 2007, 37, 1059-1066. [ Links ]
8 X. Fan, X. Hu, X. Zhang and J. Wang, Can. J. Chem., 2005, 83, 16-20. [ Links ]
9 X.-S. Fan, Y.-Z. Li, X.-Y. Zhang, X.-Y. Hu and J.-J. Wang, Chin. J. Org. Chem, 2005, 25, 1482-1486. [ Links ]
10 J.-J. Ma, J.-C. Li, R.-X. Tang, X. Zhou, Q.-H. Wu, C. Wang, M.-M. Zhang and Q. Li, Chin. J. Org. Chem., 2007, 27, 640-642. [ Links ]
11 G.I. Shakibaei, P. Mirzaei and A. Bazgir, Appl. Catal. A: Gen., 2007, 325, 188-192. [ Links ]
12 B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth and L. Nagarapu, Catal. Commun., 2007, 8, 535-538. [ Links ]
13 M. Seyyedhamzeh, P. Mirzaei and A. Bazgir, Dyes Pigments, 2008, 76, 836-839. [ Links ]
14 A. John, P.J.P. Yadav and S. Palaniappan, J. Mol. Catal. A: Chem., 2006, 248, 121-125. [ Links ]
15 S. Kantevari, R. Bantu and L. Nagarapu, J. Mol. Catal. A: Chem., 2007, 269, 53-57. [ Links ]
16 T.-S. Jin, J.-S. Zhang, A.-Q.Wang and T.-S. Li, Synth. Commun., 2005, 35, 2339-2345. [ Links ]
17 B. Das, P. Thirupathi, I. Mahender, VS. Reddy and Y.K. Rao, J. Mol. Catal. A: Chem., 2006, 247, 233-239. [ Links ]
18 Z.-H. Zhang and X.-Y. Tao, Aust. J. Chem., 2008, 61, 77-79. [ Links ]
19 S. Kantevari, R. Bantu and L. Nagarapu, Arkivoc, 2006, 16, 136-148. [ Links ]
20 T.-S. Jin, J.-S. Zhang, J.-C. Xiao, A.-Q. Wang and T.-S. Li, Synlett., 2004, 866-870. [ Links ]
21 T.-S. Jin, J.-S. Zhang, J.-C. Xiao, A.-Q. Wang and T.-S. Li, Ultrason. Sonochem., 2006, 13, 220-224. [ Links ]
22 D.-Q. Shi, Q.-Y. Zhuang J. Chen, X.-S. Wang, S.-J. Tu and H.-W. Hu, Chin. J. Org. Chem., 2003, 23, 694-697. [ Links ]
23 T.-S. Jin, J.-S. Zhang, A.-Q. Wang and F.-S. Zhang, Chin. J. Org. Chem., 2005, 25, 335-338. [ Links ]
24 G. Karthikeyan andA. Pandurangan, J. Mol. Catal. A: Chem., 2009, 311, 36-45. [ Links ]
25 (a) J.-J. Ma, X. Zhou, X.-H. Zhang, C. Wang, Z. Wang, J.-C. Li and Q. Li, Aust. J. Chem., 2007, 60, 146-148; [ Links ] (b) M. Dabiri, M. Baghbanzadeh and E. Arzroomchilar, Catal. Commun., 2008, 9, 939-942. [ Links ]
26 S.-J. Tu, J.-F. Zhou, Z.-S. Lu, X. Deng, D.-Q. Shi and S.-H. Wang, Synth. Commun., 2002, 32, 3063-3067. [ Links ]
27 S.-J. Tu, Y. Gao, X.-H. Liu, S.-F. Tang and X.-J. Qiu, Chin. J. Org. Chem, 2001, 21, 1164-1167. [ Links ]
28 (a) P.A. Grieco, Organic Synthesis in Water, Blackie Academic and Professional, London, UK, 1998; [ Links ] (b) Z.P. Demko and K.B. Sharpless, J. Org. Chem., 2001, 66, 7945-7950; [ Links ] (c) C. J. Li, Chem. Rev., 2005, 105, 3095-3166; [ Links ] (d) S. Narayan, J. Muldoon, M.G. Finn, V.V. Fokin, H.C. Kolb and K.B. Sharpless, Angew. Chem. Int. Edit. Engl., 2005, 44, 3275-3279; [ Links ] (e) U.M. Lindstrom, Chem. Rev., 2002, 102, 2751-2772; [ Links ] (f) C. Wei and C.J. Li, J. Am. Chem. Soc., 2003, 125, 9584-9585. [ Links ]
29 (a) J. Azizian, A.A. Mohammadi, A.R. Karimi and M.R. Mohamma-dizadeh, J. Org. Chem., 2005, 70, 350-352; [ Links ] (b) M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary and A.A. Mohammadi, Tetrahedron Lett., 2005, 46, 6123-6126; [ Links ] (c) J. Azizian, A.A. Mohammadi, A.R. Karimi and M.R. Mohammadizadeh, Appl. Catal. A. General, 2006, 300, 85-88; [ Links ] (d) M. Dabiri, M. Baghbanzadeh, S. Kiani and Y. Vakilzadeh, Monatsh. Chem., 2007, 138, 997-999; [ Links ] (e) M. Dabiri, M. Baghbanzadeh and M. Bahramnejad, Monatsh. Chem., 2007, 138, 1253-1255; [ Links ] (f) M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh and E. Arzroomchilar, Bioorg. Med. Chem. Lett., 2008, 18, 436-438; [ Links ] (g) D. Mahajan, T. Nagvi, R.L. Sharma and K.K. Kapoor, Aust. J. Chem., 2008, 61, 159-162; [ Links ] (h) A.A. Mohammadi, M. Mivechi and H. Kefayati, Monatsh. Chem., 2008, 139, 935-937. [ Links ]
30 (a) S.S. Pawar, D.V. Dekhane, M.S. Shingare and S.N. Thore, Aust. J. Chem., 2008, 61, 905-909; [ Links ] (b) K.F. Shelke, S.B. Sapkal and M.S. Shingare, Chin. Chem. Lett., 2009, 20, 283-287; [ Links ] (c) S.S. Sonar, S.A. Sadaphal, A.H. Kategaonkar, R.U. Pokalwar, B.B. Shingate and M.S. Shingare, Bull. Korean Chem. Soc., 2009, 30, 825-828; [ Links ] (d) K.F. Shelke, S.B. Sapkal, S.S. Sonar, B.R. Madje, B.B. Shingate and M.S. Shingare, Bull. Korean Chem. Soc., 2009, 30, 1057-1060. [ Links ]
Received 24 December 2009
Revised 3 March 2010
Accepted 29 March 2010
* To whom correspondence should be addressed. E-mail: balumadje@yahoo.com.