Solvent-free synthesis of 2H-indazolo[2,1-b] phthalazine-triones promoted by cavitational phenomenon using iodine as catalyst

Anitha Varghese; Aatika Nizam; Rajani Kulkarni; Louis George

doi:10.5155/eurjchem.4.2.132-137.746

PDF

Published: Jun 30, 2013

DOI: https://doi.org/10.5155/eurjchem.4.2.132-137.746

Keywords:

Iodine, Dimedone, Phthalhydrazide, Aromatic aldehydes, Cavitational chemistry, 2H-Indazolo[2, 1-b]phthalazine-triones

Section

Research Article

Issue

Vol. 4 No. 2 (2013): June 2013

Dates

Received 2013-02-11
Accepted 2013-03-13
Published 2013-06-30

Anitha Varghese

Department of Chemistry, Christ University, Bangalore, 560 029, India

Aatika Nizam

Department of Chemistry, Christ University, Bangalore, 560 029, India

Rajani Kulkarni

Department of Chemistry, Christ University, Bangalore, 560 029, India

Louis George

Department of Chemistry, Christ University, Bangalore, 560 029, India

Abstract

An environmentally benign, simple and efficient protocol for the synthesis of 2H-indazolo[2,1-b] phthalazine-triones by condensation of phthalhydrazide, aromatic aldehydes and dimedone under solvent-free ultrasound assisted conditions employing a safe, readily available iodine as catalyst has been described. This process is a valuable addition as it devoids the use of any solvent and takes place in short duration of time giving good yield of the products.

This Abstract was viewed 2976 times |

Article PDF downloaded 1840 times

How to Cite

(1)

Varghese, A.; Nizam, A.; Kulkarni, R.; George, L. Solvent-Free Synthesis of 2H-indazolo[2,1-B] Phthalazine-Triones Promoted by Cavitational Phenomenon Using Iodine As Catalyst. Eur. J. Chem. 2013, 4, 132-137.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Sayyafi, M.; Seyyedhamzeh, M.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2008, 64, 2375-2378.
http://dx.doi.org/10.1016/j.tet.2008.01.006

[2]. Franklin, E. C. Chem. Rev. 1935, 16, 305-361.
http://dx.doi.org/10.1021/cr60055a001

[3]. Bergstrom, F. W. Chem. Rev. 1944, 35, 77-277.
http://dx.doi.org/10.1021/cr60111a001

[4]. Lichtenthaler, F. W. Acc. Chem. Res. 2002, 35, 728-737.
http://dx.doi.org/10.1021/ar010071i
PMid:12234202

[5]. Litvinov, V. P. Russ. Chem. Rev. 2003, 72, 69-85
http://dx.doi.org/10.1070/RC2003v072n01ABEH000764

[6]. Xu, Y.; Guo, Q-X. Heterocycles 2004, 63, 903-974.
http://dx.doi.org/10.3987/REV-03-574

[7]. Vaughan, W. R. Chem. Rev. 1948, 43, 447-508.
http://dx.doi.org/10.1021/cr60136a003
PMid:18105910

[8]. Clement, R. A. J. Org. Chem. 1960, 25, 1724-1727.
http://dx.doi.org/10.1021/jo01080a011

[9]. Heine, H. W.; Henrie, R.; Heitz, L.; Kovvali, S. R. J. Org. Chem. 1974, 39, 3187-3191.
http://dx.doi.org/10.1021/jo00936a001

[10]. Heine, H. W.; Baclawski, L. M.; Bonser, S. M.; Wachob, G. D. J. Org. Chem. 1976, 41, 3229-3232.
http://dx.doi.org/10.1021/jo00882a002

[11]. Sheradsky, T.; Moshenberg, R. J. Org. Chem. 1986, 51, 3123-3125.
http://dx.doi.org/10.1021/jo00366a008

[12]. Jungheim, L. N.; Sigmund, S. K. J. Org. Chem. 1987, 52, 4007-4013.
http://dx.doi.org/10.1021/jo00227a013

[13]. Indelicato, J. M.; Pasini, C. E. J. Med. Chem. 1988, 31, 1227-1230.
http://dx.doi.org/10.1021/jm00401a026

[14]. Kappe, T.; Kos, C. Synthesis 1989, 629-630.
http://dx.doi.org/10.1055/s-1989-27341

[15]. Turk, C.; Svete, J.; Stanovnik, B.; Goli, C. L.; Grdadolnik, S.; Golobi, C. A.; Seli Helv, C. L. Chim. Acta. 2001, 84, 146-156.
http://dx.doi.org/10.1002/1522-2675(20010131)84:1<146::AID-HLCA146>3.3.CO;2-Z

[16]. Clark, M. P.; Laughlin, S. K.; Laufersweiler, M. J.; Bookland, R. G.; Brugel, T. A.; Golebiowski, A.; Sabat, M. P.; Townes, J. A.; VanRens, J. C.; Djung, J. F.; Natchus, M. G.; De, B.; Hsieh, L. C.; Xu, S. C.; Walter, R. L.; Mekel, M. J.; Heitmeyer, S. A.; Brown, K. K.; Juergens, K.; Taiwo, Y. O.; Janusz, M. J. J. Med. Chem. 2004, 47, 2724-2727.
http://dx.doi.org/10.1021/jm049968m
PMid:15139749

[17]. Nomoto, Y.; Obase, H.; Takai, H.; Teranishi, M.; Nakamura, J.; Kubo, K. Chem. Pharm. Bull. (Tokyo) 1990, 38, 2179-2183.
http://dx.doi.org/10.1248/cpb.38.2179

[18]. Watanabe, N.; Kabasawa, Y.; Takase, Y.; Matsukura, M.; Miyazaki, K.; Ishihara, H.; Kodama, K.; Adachi, H. J. Med. Chem. 1998, 41, 3367-3372.
http://dx.doi.org/10.1021/jm970815r
PMid:9719589

[19]. Kim, J. S.; Rhee, H. K.; Park, H. J.; Lee, S. K.; Lee, C. O.; Park Choo, H. Y. Bioorg. Med. Chem. 2008, 16, 4545-4550.
http://dx.doi.org/10.1016/j.bmc.2008.02.049
PMid:18321715

[20]. El-Sakka, S. S.; Soliman, A. H.; Imam, A. M. Afinidad 2009, 66, 167-172.

[21]. Ryu, C. K.; Park, R. E.; Ma, M. Y.; Nho, J. H. Bioorg. Med. Chem. Lett. 2007, 17, 2577-2580.
http://dx.doi.org/10.1016/j.bmcl.2007.02.003
PMid:17320386

[22]. Li, J.; Zhao, Y. F.; Yuan, X. Y.; Xu, J. X.; Gong, P. Molecules 2006, 11, 574-582.
http://dx.doi.org/10.3390/11070574
PMid:17971729

[23]. Sinkkonen, J.; Ovcharenko, V.; Zelenin, K. N.; Bezhan, I. P.; Chakchir, B. A.; Al-Assar, F.; Pihlaja, K. Eur. J. Org. Chem. 2002, 13, 2046-2053.
http://dx.doi.org/10.1002/1099-0690(200207)2002:13<2046::AID-EJOC2046>3.0.CO;2-C

[24]. Grasso, S.; DeSarro, G.; Micale, N.; Zappala, M.; Puia, G.; Baraldi, M.; Demicheli, C. J. Med. Chem. 2000, 43, 2851-2859.
http://dx.doi.org/10.1021/jm001002x

[25]. Sheradsky, T.; Moshenberg, R. J. Org. Chem. 1986, 51, 3123-3125.
http://dx.doi.org/10.1021/jo00366a008

[26]. Heine, H. W.; Baclawski, L. M.; Bonser, S. M.; Wachob, G. D. J. Org. Chem. 1976, 41, 3229-3232.
http://dx.doi.org/10.1021/jo00882a002

[27]. Ramtohup, Y. K.; James, M. N. G.; Vederas, J. C. J. Org. Chem. 2002, 67, 3169-3178.
http://dx.doi.org/10.1021/jo0157831

[28]. Liu, L. P.; Lu, J. M.; Shi, M. Org. Lett. 2007, 9, 1303-1306.
http://dx.doi.org/10.1021/ol070178r
PMid:17348667

[29]. Csampai, A.; Kormendy, K.; Ruff, F. Tetrahedron 1991, 47, 4457-4464.
http://dx.doi.org/10.1016/S0040-4020(01)87114-3

[30]. Amarasekara, A. S.; Chandrasekara, S. Org. Lett. 2002, 4, 773-775.
http://dx.doi.org/10.1021/ol017256+
PMid:11869124

[31]. Hwang, J. Y.; Choi, H. S.; Gong, Y. D. Tetrahedron Lett. 2005, 46, 3107-3110.
http://dx.doi.org/10.1016/j.tetlet.2005.02.154

[32]. Fazaeli, R.; Aliyan, H.; Fazaeli, N. Open Catal. J. 2010, 3, 14-18.
http://dx.doi.org/10.2174/1876214X01003010014

[33]. Khurana, J. M.; Magoo, D. Tetrahedron Lett. 2009, 50, 7300-7303.
http://dx.doi.org/10.1016/j.tetlet.2009.10.032

[34]. Vaghei, R. G.; Karimi-Nami, R.; Toghraei-Semiromi, Z.; Amiri, M.; Ghavidel, M. Tetrahedron 2011, 67, 1930-1937.
http://dx.doi.org/10.1016/j.tet.2011.01.024

[35]. Shukla, G.; Verma, R. K.; Verma, G. K.; Singh, M. S. Tetrahedron Lett. 2011, 52, 7195-7198.
http://dx.doi.org/10.1016/j.tetlet.2011.10.136

[36]. Shekouhy, M.; Hasaninejad, A. Ultrasonics Sonochemistry 2012, 19, 307-313.
http://dx.doi.org/10.1016/j.ultsonch.2011.07.011
PMid:21868275

[37]. Mosaddegh, E.; Hassankhani, A. Tetrahedron Lett. 2011, 52, 488-490.
http://dx.doi.org/10.1016/j.tetlet.2010.08.099

[38]. Nagarapu, L.; Bantu, R.; Hari Babu, M. J. Heterocyclic Chem. 2009, 46, 728-731.
http://dx.doi.org/10.1002/jhet.135

[39]. Shaterian, H. R.; Ghashang, M.; Feyzi, M. Appl Catal A Gen 2008, 345, 128-133.
http://dx.doi.org/10.1016/j.apcata.2008.04.032

[40]. Shaterian, H. R.; Khorami, F.; Amirzadeh, A.; Doostmohammadi, R.; Ghashang, M. J. Iran. Chem. Res. 2009, 2, 57-62.

[41]. Shaterian, H. R.; Hosseinian, A.; Ghashang, M. Arkivoc 2009, 2, 59-67.
http://dx.doi.org/10.3998/ark.5550190.0010.207

[42]. Toure, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439-4486.
http://dx.doi.org/10.1021/cr800296p
PMid:19480390

[43]. Bondock, S.; Fadaly, W.; Metwally, M. A. J. Sulfur Chem. 2009, 30, 74-107.
http://dx.doi.org/10.1080/17415990802588033

[44]. Ganem, B. Acc. Chem. Res. 2009, 42, 463-472.
http://dx.doi.org/10.1021/ar800214s
PMid:19175315 PMCid:2765544

[45]. Domling, A. Chem. Rev. 2006, 106, 17-89.
http://dx.doi.org/10.1021/cr0505728
PMid:16402771

[46]. Gerencser, J.; Dormon, G.; Darvas, F. QSAR Comb. Sci. 2006, 25, 439-448.
http://dx.doi.org/10.1002/qsar.200540212

[47]. Ramon, D. J.; Yus, M. Angew. Chem. Int. 2005, 44, 1602-1634.
http://dx.doi.org/10.1002/anie.200460548
PMid:15719349

[48]. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80.
http://dx.doi.org/10.2174/0929867033368600
PMid:12570721

[49]. Basso, A.; Banfi, L.; Riva, R.; Guanti, G. J. Org. Chem. 2005, 70, 575-579.
http://dx.doi.org/10.1021/jo048389m
PMid:15651804

[50]. Staben, S. T.; Blaquiere, N. Angew. Chem. Int. Ed. 2010, 49, 325-328.
http://dx.doi.org/10.1002/anie.200905897
PMid:19998301

[51]. Yue, T.; Wang, M. X.; Wang, D. X.; Masson, G.; Zhu, J. J. Org. Chem. 2009, 74, 8396-8399.
http://dx.doi.org/10.1021/jo9017765
PMid:19788173

[52]. Trofimov, B. A.; Andriyankova, L. V.; Belyaeva, K. V.; Malkina, A. G.; Nikitina, L. P.; Afonin, A. V.; Ushakov, I. A. Eur. J. Org. Chem. 2010, 9, 1772-1777.
http://dx.doi.org/10.1002/ejoc.200901397

[53]. Ma, N.; Jiang, B.; Zhang, G.; Tu, S. J.; Wever, W.; Li, G. Green Chem 2010, 12, 1357-1361.
http://dx.doi.org/10.1039/c0gc00073f

[54]. Kategaonkar, A. H.; Sonar, S. S.; Shelke, K. F.; Shingate, B. B.; Shingare, M. S. Org. Commun. 2010, 3:1, 1-7.

[55]. Kumar, A.; Maurya, R. A. Tetrahedron 2007, 63, 1946-1952.
http://dx.doi.org/10.1016/j.tet.2006.12.074

[56]. Ali, S. S. Archives of Applied Science Research 2010, 2, 121-125.

[57]. Kidwai, M.; Mothsra, P.; Bansal, V.; Goyal, R. Mont. Fur. Chem. 2006, 137, 1189-1194.
http://dx.doi.org/10.1007/s00706-006-0518-9

[58]. Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959-1961.
http://dx.doi.org/10.1016/S0040-4039(03)00032-7

[59]. Singh, A. K.; Shukla, S. K.; Quraishi, M. A. J. Mater. Environ. Sci. 2011, 2, 403-406.

[60]. USEPA website, EPA's Green Chemistry Program, http://www.epa.gov/opptintr/greenchemistry/index.htm

[61]. Singh, A. K.; Shukla, S. K.; Ahamad, I.; Quraishi, M. A. J. Heterocycl. Chem. 2009, 46, 571-574.
http://dx.doi.org/10.1002/jhet.131

[62]. Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press: New York, 1998.
PMid:11270332

[63]. Feng, R.; Li, H. M. Sheng Huexue Jiqi Yingyong; Anhui Science & Technology Press, Hefei, 1992.

[64]. Wang, L. M.; Tian, H.; Jingxi Youji Hecheng Xinfangfa; Chemical Industry Press: Beijing, 2004, pp. 396.

[65]. Li, J. T.; Yang, W. Z.; Wang, S. X.; Li, S. H.; Li, T. S. Ultrason. Sonochem. 2002, 9, 237-239.
http://dx.doi.org/10.1016/S1350-4177(02)00079-2

[66]. Mason, T. J. Advances in Sonochemistry, JAI Press: London, 1990.

[67]. Shibata, K.; Katsuyama, I.; Matsui, M.; Muramatsu, H. Bull. Chem. Soc. Jpn. 1990, 63, 3710-3712.
http://dx.doi.org/10.1246/bcsj.63.3710

[68]. Nandurkar, N. S. Synthetic Organic Sonochemistry, Plenum Press: New York, 1998.

[69]. Li, J. T.; Chen, G. F.; Yang, W. Z.; Li, T. S. Ultrason. Sonochem. 2003, 10, 123-126.
http://dx.doi.org/10.1016/S1350-4177(02)00159-1

[70]. Li, J. T.; Chen, G. F.; Xu, W. Z.; Li, T. S. Ultrason. Sonochem. 2003, 10, 115-118.
http://dx.doi.org/10.1016/S1350-4177(02)00134-7

[71]. Ding, L.; Wang, W.; Zhang, A. Ultrason. Sonochem. 2007, 14, 563-567.
http://dx.doi.org/10.1016/j.ultsonch.2006.09.008
PMid:17113334

[72]. Kappe, C. O. Tetrahedron 1993, 49, 6937-6963.
http://dx.doi.org/10.1016/S0040-4020(01)87971-0

[73]. DoÈmling, A.; Herdtweck, F.; Ugi, I. Acta Chem. Scand. 1998, 52, 107-113.
http://dx.doi.org/10.3891/acta.chem.scand.52-0107

[74]. Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366-374.
http://dx.doi.org/10.1055/s-1999-2612

[75]. Hong-Juan, W.; Xiao-Nan, Z.; Zhan-Hui, Z. Monatsh. Chem. 2010, 141, 425-430.
http://dx.doi.org/10.1007/s00706-010-0283-7

[76]. Timothy, J. M. Chemical Society Reviews, 1997, 26, 443-451.
http://dx.doi.org/10.1039/cs9972600443

[77]. Richards, W. T.; Loomis, A. L. J. Am. Chem. Soc. 1927, 49, 3086-3100;
http://dx.doi.org/10.1021/ja01411a015

[78]. Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press; New York, 1998.
PMid:11270332

Supporting Agencies

Centre for Research, Christ University, Bangalore, India

Most read articles by the same author(s)

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2025 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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics