European Journal of Chemistry

A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives



Main Article Content

Pradeep Lokhande
Kamal Hasanzadeh
Shankaraiah Guruvaiah Konda

Abstract

A convenient protocol for the efficient synthesis of 2-arylpyrazolo[4,3-c]coumarins is described. The synthesis route involves molecular iodine catalyzed oxidative cyclization of 1-phenyl-3-(2'-hydroxyaryl)-4-formyl pyrazoles in dimethylsulfoxide. During the lactonisation of 4-formylpyrazoles, we found that iodine was incorporated into the unsubstituted O/P position of the 3-(2'-hydroxyaryl) group. Under similar conditions o-allyloxy derivative of pyrazoles gave same corresponding lactone derivatives by deallylation, lactonisation, and iodination in one step.

2_2_223_228_800


icon graph This Abstract was viewed 3156 times | icon graph Article PDF downloaded 1061 times

How to Cite
(1)
Lokhande, P.; Hasanzadeh, K.; Konda, S. G. A Novel and Efficient Approach for the Synthesis of New Halo Substituted 2-arylpyrazolo[4,3-C] Coumarin Derivatives. Eur. J. Chem. 2011, 2, 223-228.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. O'Rielly, R. A.; Pool, J. G.; Aggeler, P. M. Ann. NY Acad. Sci. 1968, 151, 913-931.
PMid:4189970

[2]. Samama, M. J. Mal. Vasc. 2001, 26, 165-168.

[3]. Spino, C.; Dodier, M.; Sotheeswaran, S. Bioorg. Med. Chem. Lett. 1998, 8, 3475-3478.
doi:10.1016/S0960-894X(98)00628-3

[4]. Borges, F.; Roleira, F.; Milhazez, N.; Santana, L.; Uriarte, E. Curr. Med. Chem. 2005, 12, 887-916.
doi:10.2174/0929867053507315
PMid:15853704

[5]. Symeonidis, T.; Chamilos, M.; Latina, D. J. H.; Kallitsakism, M.; Litinas, K. E. Bioorg. Med. Chem. Lett. 2009, 19, 1139-1142.
doi:10.1016/j.bmcl.2008.12.098

[6]. Burlison, J. A.; Neckers, L.; Smith, A. B.; Maxwell, A.; Blagg, B. S. J. J. Am. Chem. Soc. 2006, 128, 15529-15536.
doi:10.1021/ja065793p
PMid:17132020

[7]. Donnelly, A.; Blagg, B. S. Curr. Med. Chem. 2008, 15, 2702-2717.
doi:10.2174/092986708786242895
PMid:18991631 PMCid:2729083

[8]. Timil, M. C.; Orallo, F.; Santana, L.; Uriarte, E. Bioorg. Med. Chem. Lett. 2002, 12, 783-786.
doi:10.1016/S0960-894X(02)00015-X

[9]. Ghate, M.; Manohar, D.; Kulkarni, V., Shobha, R.; Kattimani, S. Y. Eur. J. Med. Chem. 2003, 38, 297-302.
doi:10.1016/S0223-5234(03)00016-3

[10]. Kempen, I.; Papapostolou, D.; Thierry, N.; Pochet, L.; Counerotte, S.; Masereel, B.; Foidar, J-M.; Ravaukx, M. R.; Noel, A.; Pirotte, B. Br. J. Cancer 2003, 88, 1111-1118.
doi:10.1038/sj.bjc.6600856
PMid:12671713 PMCid:2376372

[11]. Sahidhara, K. V.; Kumar, A.; Kumar, M.; Sarkar, J.; Sinha, S. Bioorg. Med. Chem. Lett. 2010, 20, 7205-7211.
doi:10.1016/j.bmcl.2010.10.116

[12]. Panteleon, V.; Kostakis, I. K.; Markos, P.; Pouli, N.; Andreadou, I. Bioorg. Med. Chem. 2008, 18, 5781-5784.
doi:10.1016/j.bmcl.2008.09.065

[13]. Dawane, B. S.; Konda, S. G.; Badade, R. G.; Bhosale, R. B. J. Heterocycl. Chem. 2010, 47, 237-241.
doi:10.1002/jhet.413

[14]. Rajagopal, R.; Sheno, U. V.; Padmanabhan, S.; Sequeira, S.; Seshadri, S, Dyes Pigments 1990, 13, 167-175.
doi:10.1016/0143-7208(90)80016-I

[15]. Stadlbauer, W.; Hojas, G. J. Heterocycl. Chem. 2004, 41, 681-690.
doi:10.1002/jhet.5570410505

[16]. Strakova, I.; Petova, M.; Belyakov, S.; Strakais, A.; Chem. Heterocycl. Comp. 2003, 39, 1608-1616.
doi:10.1023/B:COHC.0000018338.41222.a2

[17]. Summers, J. B.; Gunn, B. P.; Martin, J. G.; Mazdiyasni, H.; Stewart, A. O.; Young, P. P.; Goetze, A. M.; Bouka, J. B.; Deyr, R. D. J. Med. Chem. 1988, 31, 3-5.
doi:10.1021/jm00396a002
PMid:3336029

[18]. Yadav, J. S.; Reddy, B. V-S.; Thrimurtula, N.; Reddy, N. M.; Prased, A. R. Tetrahedron Lett. 2008, 49, 2031- 2033.
doi:10.1016/j.tetlet.2008.01.017

[19]. Rao, W.; Tay, A. H. L.; Goh, P. J.; Choy, J. M. L.; Ke, J. K.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 122-126.
doi:10.1016/j.tetlet.2007.11.005

[20]. Srihari, P.; Dinesh, C.; Bhunia, P.; Sreedhar, S. S.; Mandal, J.; Reddy, J. S. S.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 8120-8124.
doi:10.1016/j.tetlet.2007.09.123

[21]. Sun, G.; Wang, Z. Tetrahedron Lett. 2008, 49, 4929-4932.
doi:10.1016/j.tetlet.2008.05.146

[22]. Wang, X-S.; Zhou, J.; Yin, M. Y.; Yang, K.; Tu. S. J. J. Comb. Chem. 2010, 12, 266-269.
doi:10.1021/cc900165j
PMid:20067233

[23]. Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 4509-4512.
doi:10.1016/j.tetlet.2006.03.123

[24]. Lin, X.; Dai, X.; Mao, Z.; Wang, Y. Tetrahedron 2009, 65, 9233-9237.
doi:10.1016/j.tet.2009.09.007

[25]. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. Org. Lett. 2006, 8, 2491-2494.
doi:10.1021/ol060590r
PMid:16737296

[26]. Wang, J.; Xu, F. X.; Lin, X. F.; Wang, Y. G. Tetrahedron Lett. 2008, 49, 5208-5210.
doi:10.1016/j.tetlet.2008.06.024

[27]. Lin, X. F.; Cui, S. L.; Wang, Y. G. Tetrahedron Lett. 2006, 47, 3127-3130.
doi:10.1016/j.tetlet.2006.02.136

[28]. Sun, J.; Dong, Y.; Cao, L.; Wang, X.; Wang, S.; Hu, Y. J. Org. Chem. 2004, 69, 8932-8934.
doi:10.1021/jo0486239
PMid:15575776

[29]. Lokhande, P. D.; Waghmare B. Y.; Sakate S. S. Indian J. Chem, 2005, 44B, 2338-2342.

[30]. Lokhande, P. D.; Sakte, S, S.; Taksande K, N.; Navghare, B. Tetrahedron Lett. 2005, 46, 1573-1574.
doi:10.1016/j.tetlet.2004.12.041

[31]. Lokhande, P. D.; Ghiya B. J. J. Indian Chem. Soc. 1991, 68, 412-413.

[32]. Vogel's Text book Practical Organic Chemistry, 5th ed, Longman, London, 1989.

[33]. Alkhathlan, H. Z. Tetrahedron, 2003, 59, 8163-8170.
doi:10.1016/j.tet.2003.08.044

[34]. Rathelot, P.; Azas, N.; Kashef, H. E.; Delmas, F.; Giorgio, C. D.; David, P. T.; Maldonado, J.; Vanelle, P. Eur. J. Med. Chem. 2002, 37, 671-679.
doi:10.1016/S0223-5234(02)01388-0

Supporting Agencies

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).