European Journal of Chemistry

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



Main Article Content

Anitha Varghese
Aatika Nizam
Rajani Kulkarni
Louis George

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.

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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.

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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

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