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http://dx.doi.org/10.5012/bkcs.2013.34.11.3415

Synthesis of 1H-Indol-3-ylpyrazole Derivatives from 1,3,5-Triketones and Arylhydrazines: One-Pot Construction of Pyrazole and Indole Rings  

Kim, Sung Hwan (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Lee, Sangku (Immune Modulator Research Center, KRIBB)
Kim, Se Hee (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Kim, Ko Hoon (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Kim, Jae Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Publication Information
Abstract
The reaction of 1,3,5-triketones and arylhydrazines provided indolylpyrazole derivatives in a one-pot reaction in good to moderate yields. Both the pyrazole and indole rings were constructed simultaneously with phenylhydrazine, $RCOCH_2CO$- moiety for the pyrazole and the remaining -$CH_2COR$ part for the indole ring.
Keywords
Indolylpyrazole; 1,3,5-Triketones; Fischer indole synthesis;
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1 Zhang, D.; Wang, G.; Zhao, G.; Xu, W.; Huo, L. Eur. J. Med. Chem. 2011, 46, 5868-5877.   DOI   ScienceOn
2 Pierce, L. T.; Cahill, M. M.; McCarthy, F. O. Tetrahedron 2011, 67, 4601-4611.   DOI   ScienceOn
3 Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H.-H.; Cirrincione, G. Bioorg. Med. Chem. 2010, 18, 4524-4529.   DOI   ScienceOn
4 Zhang, N.; Ayral-Kaloustian, S.; Anderson, J. T.; Nguyen, T.; Das, S.; Venkatesan, A. M.; Brooijmans, N.; Lucas, J.; Yu, K.; Hollander, I.; Mallon, R. Bioorg. Med. Chem. Lett. 2010, 20, 3526-3529.   DOI   ScienceOn
5 Velankar, A. D.; Quintini, G.; Prabhu, A.; Weber, A.; Hunaeus, G.; Voland, B.; Wuest, M.; Orjeda, C.; Harel, D.; Varghese, S.; Gore, V.; Patil, M.; Gayke, D.; Herdemann, M.; Heit, I.; Zaliani, A. Bioorg. Med. Chem. 2010, 18, 4547-4559.   DOI   ScienceOn
6 Diana, P.; Carbone, A.; Barraja, P.; Martorana, A.; Gia, O.; DallaVia, L.; Cirrincione, G. Bioorg. Med. Chem. Lett. 2007, 17, 6134-6137.   DOI   ScienceOn
7 Sivaprasad, G.; Perumal, P. T.; Prabavathy, V. R.; Mathivanan, N. Bioorg. Med. Chem. Lett. 2006, 16, 6302-6305.   DOI   ScienceOn
8 Reddy, M. V. R.; Billa, V. K.; Pallela, V. R.; Mallireddigari, M. R.; Boominathan, R.; Gabriel, J. L.; Reddy, E. P. Bioorg. Med. Chem. 2008, 16, 3907-3916.   DOI   ScienceOn
9 Khan, T. A.; Kumar, S.; Venkatesh, C.; Ila, H. Tetrahedron 2011, 67, 2961-2968.   DOI   ScienceOn
10 Delaunay, T.; Genix, P.; Es-Sayed, M.; Vors, J.-P.; Monteiro, N.; Balme, G. Org. Lett. 2010, 12, 3328-3331.   DOI   ScienceOn
11 Delaunay, T.; Es-Sayed, M.; Vors, J.-P.; Monteiro, N.; Balme, G. Eur. J. Org. Chem. 2011, 3837-3848.
12 Bobko, M. A.; Kaura, A. C.; Evans, K. A.; Su, D.-S. Org. Lett. 2012, 14, 3906-3908.   DOI   ScienceOn
13 Stansfield, I.; Pompei, M.; Conte, I.; Ercolani, C.; Migliaccio, G.; Jairaj, M.; Giuliano, C.; Rowley, M.; Narjes, F. Bioorg. Med. Chem. Lett. 2007, 17, 5143-5149.   DOI   ScienceOn
14 Pintori, D. G.; Greaney, M. F. J. Am. Chem. Soc. 2011, 133, 1209-1211.   DOI   ScienceOn
15 Nayak, M.; Batra, S. Eur. J. Org. Chem. 2012, 3677-3683.
16 Usachev, B. I.; Obydennov, D. L.; Kodess, M. I.; Roschenthaler, G.-V.; Sosnovskikh, V. Y. Russ. Chem. Bull. Int. Ed. 2009, 58, 1248-1252.   DOI
17 Usachev, B. I.; Obydennov, D. L.; Roschenthaler, G.-V.; Sosnovskikh, V. Y. J. Fluorine Chem. 2012, 137, 22-26.   DOI   ScienceOn
18 Usachev, B. I.; Obydennov, D. L.; Sosnovskikh, V. Y. J. Fluorine Chem. 2012, 135, 278-284.   DOI   ScienceOn
19 Usachev, B. I.; Obydennov, D. L.; Kodess, M. I.; Sosnovskikh, V. Y. Tetrahedron Lett. 2009, 50, 4446-4448.   DOI   ScienceOn
20 Sechi, M.; Innocenti, A.; Pala, N.; Rogolino, D.; Carcelli, M.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2012, 22, 5801-5806.   DOI   ScienceOn
21 Jukic, M.; Cetina, M.; Pavlovic, G.; Rapic, V. Struct. Chem. 1999, 10, 85-90.   DOI   ScienceOn
22 Kim, S. H.; Lee, S.; Kim, S. H.; Lim, J. W.; Kim, J. N. Tetrahedron Lett. 2012, 53, 4979-4983.   DOI   ScienceOn
23 Dandia, A.; Rani, B.; Saha, M. Indian J. Chem. Technol. 1998, 5, 159-162.
24 Qu, J.; Kumar, N.; Alamgir, M.; Black, D. StC. Tetrahedron Lett. 2009, 50, 5628-5630.   DOI   ScienceOn
25 Black, D. StC.; Deb-Das, R. B.; Kumar, N. Aust. J. Chem. 1992, 45, 611-621.   DOI
26 Butin, A. V.; Uchuskin, M. G.; Pilipenko, A. S.; Serdyuk, O. V.; Trushkov, I. V. Tetrahedron Lett. 2011, 52, 5255-5258.   DOI   ScienceOn
27 Dandia, A.; Sehgal, V.; Upreti, M. Phosphorous, Sulfur and Silicon 1995, 105, 93-99.   DOI   ScienceOn
28 Saadeh, H. A.; Abu Shairah, E. A.; Charef, N.; Mubarak, M. S. J. Appl. Polym. Sci. 2012, 124, 2717-2724.   DOI   ScienceOn
29 El-Kholy, I. E.-S.; Rafla, F. K.; Soliman, G. J. Chem. Soc. 1962, 1857-1863.   DOI
30 Chou, S.-Y.; Chen, C.-J.; Tsai, S.-L.; Sheu, H.-S.; Lee, G.-H.; Lai, C. K. Tetrahedron 2009, 65, 1130-1139.   DOI   ScienceOn
31 Walker, S. R.; Carter, E. J.; Huff, B. C.; Morris, J. C. Chem. Rev. 2009, 109, 3080-3098.   DOI   ScienceOn
32 Akue-Gedu, R.; Debiton, E.; Ferandin, Y.; Meijer, L.; Prudhomme, M.; Anizon, F.; Moreau, P. Bioorg. Med. Chem. 2009, 17, 4420-4424.   DOI   ScienceOn
33 Radwan, M. A. A.; El-Sherbiny, M. Bioorg. Med. Chem. 2007, 15, 1206-1211.   DOI   ScienceOn
34 Katritzky, A. R.; Abdel-Fattah, A. A. A.; Akhmedova, R. G. ARKIVOC 2005 (vi) 329-338.
35 Prekupec, S.; Makuc, D.; Plavec, J.; Suman, L.; Kralj, M.; Pavelic, K.; Balzarini, J.; De Clerq, E.; Mintas, M.; Raic-Malic, S. J. Med. Chem. 2007, 50, 3037-3045.   DOI   ScienceOn