Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(04): 562-568
DOI: 10.1055/s-0034-1379584
DOI: 10.1055/s-0034-1379584
paper
Copper(I) Iodide Catalyzed Synthesis of Fused Hexacyclic Pyrazolo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-ones under Ligand-Free Conditions
Further Information
Publication History
Received: 21 August 2014
Accepted after revision: 31 October 2014
Publication Date:
14 November 2014 (online)
Abstract
The three-component reaction of an o-halogenated benzaldehyde, 1H-indazol-6-amine, and cyclohexane-1,3-dione is described for the construction of fused hexacycles catalyzed by copper(I) iodide under ligand-free conditions. This is a domino reaction that constructs two new heterocycles and six new bonds in a one-pot reaction, and provides an efficient method for the synthesis of pyrazolo[4,5,1-de]quinolino[4,3,2-mn]acridin-14(11H)-ones in good yields.
Key words
1H-indazol-6-amine - pyrazoloquinolinoacridine - domino reaction - copper(I) iodide - ligand-freeSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379584. Included are copies of the 1H NMR and 13C NMR spectra for compounds 4a–t.
- Supporting Information
-
References
- 1a Gali R, Banothu J, Porika M, Velpula R, Hnamte S, Bavantula R, Abbagani S, Busi S. Bioorg. Med. Chem. Lett. 2014; 24: 4239
- 1b Dore A, Asproni B, Scampuddu A, Pinna GA, Christoffersen CT, Langgard M, Kehler J. Eur. J. Med. Chem. 2014; 84: 181
- 1c Colis L, Ernst G, Sanders S, Liu H, Sirajuddin P, Peltonen K, DePasquale M, Barrow JC, Laiho M. J. Med. Chem. 2014; 57: 4950
- 1d Al-Obaid AM, Abdel-Hamide SG, El-Kashef HA, Abdel-Aziz AA.-M, El-Azab AS, Al-Khamees HA, El-Subbagh HI. Eur. J. Med. Chem. 2009; 44: 2379
- 2a Belmont P, Bosson J, Godet T, Tiano M. Anti-Cancer Agents Med. Chem. 2007; 7: 139
- 2b Choudhury JR, Guddneppanavar R, Saluta G, Kucera GL, Bierbach U. J. Med. Chem. 2008; 51: 3069
- 2c Antonini I, Polucci P, Magnano A, Gatto B, Palumbo M, Menta E, Pescalli N, Martelli S. J. Med. Chem. 2003; 46: 3109
- 2d Boulanger C, Di Giorgio C, Vierling P. Eur. J. Med. Chem. 2005; 40: 1295
- 2e Antonini I. Med. Chem. Rev. 2004; 1: 267
- 2f Su T.-L, Lin Y.-W, Chou T.-C, Zhang X, Bacherikov VA, Chen C.-H, Liu LF, Tsai T.-J. J. Med. Chem. 2006; 49: 3710
- 2g Graham LA, Suryadi J, West TK, Kucera GL, Bierbach U. J. Med. Chem. 2012; 55: 7817
- 3a Bourdouxhe-Housiaux C, Colson P, Houssier C, Waring MJ, Bailly C. Biochemistry 1996; 35: 4251
- 3b Emmerson AM, Jones AM. J. Antimicrob. Chemother. 2003; 51: 13
- 3c Ketron AC, Denny WA, Graves DE, Osheroff N. Biochemistry 2012; 51: 1730
- 4a Singh K, Kaur H, Smith P, de Kock C, Chibale K, Balzarini J. J. Med. Chem. 2014; 57: 435
- 4b Yang C.-L, Tseng C.-H, Chen Y.-L, Lu C.-M, Kao C.-L, Wu M.-H, Tzeng C.-C. Eur. J. Med. Chem. 2010; 45: 602
- 4c Reddy YS. R, Afzal-Azam MD, Leonard JT, Suresh B, Chakravarthy IE. Indian J. Pharm. Sci. 2007; 69: 112
- 4d Hu B, Bernotas R, Unwalla R, Collini M, Quinet E, Feingold I, Goos-Nilsson A, Wilhelmsson A, Nambi P, Evans M, Wrobel J. Bioorg. Med. Chem. Lett. 2010; 20: 689
- 4e Eswaran S, Adhikari AV, Chowdhury IH, Pal NK, Thomas KD. Eur. J. Med. Chem. 2010; 45: 3374
- 4f Liu H, Altenbach RJ, Diaz GJ, Manelli AM, Martin RL, Miller TR, Esbenshade TA, Brioni JD, Cowart MD. Bioorg. Med. Chem. Lett. 2010; 20: 3295
- 4g Thakur GA, Kulkarni AR, Deschamps JR, Papke RL. J. Med. Chem. 2013; 56: 8943
- 5a Andrews S, Burgess SJ, Skaalrud D, Kelly JX, Peyton DH. J. Med. Chem. 2010; 53: 916
- 5b Sanchez CP, McLean JE, Stein W, Lanzer M. Biochemistry 2004; 43: 16365
- 5c Zishiri VK, Joshi MC, Hunter R, Chibale K, Smith PJ, Summers RL, Martin RE, Egan TJ. J. Med. Chem. 2011; 54: 6956
- 5d Yearick K, Ekoue-Kovi K, Iwaniuk DP, Natarajan JK, Alumasa J, de Dios AC, Roepe PD, Wolf C. J. Med. Chem. 2008; 51: 1995
- 6 Alam MM, Marella A, Akhtar M, Husain A, Yar MS, Shaquiquzzaman M, Tanwar OP, Saha R, Khanna S, Shafi S. Acta Pol. Pharm. 2013; 70: 435
- 7 Crivori P, Pennella G, Magistrelli M, Grossi P, Giusti AM. J. Chem. Inf. Model. 2011; 51: 434
- 8a Conreaux D, Mehanna N, Herse C, Lacour J. J. Org. Chem. 2011; 76: 2716
- 8b Watanabe M, Suzuki H, Tanaka Y, Ishida T, Oshikawa T, Tori-i A. J. Org. Chem. 2004; 69: 7794
- 8c Gellerman G, Rudi A, Kashman Y. Tetrahedron Lett. 1993; 34: 1823
- 9a Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 9b Ma DW, Cai Q. Acc. Chem. Res. 2008; 41: 1450
- 10a Wang Y, Chi Y, Zhang WX, Xi ZF. J. Am. Chem. Soc. 2012; 134: 2926
- 10b Bruhn T, Witterauf F, Goetz DC. G, Grimmer CT, Wuertemberger M, Radius U, Bringmann G. Chem. Eur. J. 2014; 20: 3998
- 10c Sirvent JA, Foubelo F, Yus M. J. Org. Chem. 2014; 79: 1356
- 10d Salih MQ, Beaudry CM. Org. Lett. 2013; 15: 4540
- 10e Wolter M, Klapars A, Buchwald SL. Org. Lett. 2001; 3: 3803
- 10f Chen Z, Ye C, Gao L, Wu J. Chem. Commun. 2011; 47: 5623
- 10g Hao W, Geng WZ, Zhang WX, Xi ZF. Chem. Eur. J. 2014; 20: 2605
- 10h Feng Z, Chen F, Zhang X. Org. Lett. 2012; 14: 1938
- 10i Jiang M, Li M, Wang F, Zhao Y, Zhao F, Dong X, Zhao W. Org. Lett. 2012; 14: 1420
- 10j Xiong X, Jiang Y, Ma D. Org. Lett. 2012; 14: 2552
- 10k Sang P, Xie Y, Zou J, Zhang Y. Org. Lett. 2012; 14: 3894
- 10l Zhou F, Guo J, Liu J, Ding K, Yu S, Cai Q. J. Am. Chem. Soc. 2012; 134: 14326
- 10m Xu W, Jin Y, Liu H, Jiang Y, Fu H. Org. Lett. 2011; 13: 1274