Home Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
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Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction

  • Hong Jiang , Wei Wang and Xiang-Shan Wang EMAIL logo
Published/Copyright: August 1, 2012

Abstract

A series of ethyl 5-aryl-1,2-dihydroanthra[2,1-c][2,7]naphthyridine-3(4H)-carboxylate derivatives was prepared by a three-component reaction of aromatic aldehyde, anthracen-2-amine and ethyl 4-oxopiperidine-1-carboxylate using iodine as catalyst. This iodine-catalyzed procedure has the advantages of mild reaction conditions, good yields, operational simplicity and metal-free catalyst.


Corresponding author: Xiang-Shan Wang, School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, P.R. China

We are grateful to the National Natural Science Foundation of China (20802061), the Priority Academic Program Development of Jiangsu Higher Education Institutions and Qing Lan Project (08QLT001, 10QLD008) of Jiangsu Education Committee and Graduate Foundation of Jiangsu Normal University for financial support.

References

Armstrong, D. J.; Goto, Y.; Hashihayata, T.; Kato, T.; Kelly, M. J. III.; Layton, M. E.; Lindsley, C. W.; Ogino, Y.; Onozaki, Y.; Rodzinak, K. J.; Rossi, M. A.; Sanderson, P. E.; Wang, J. B.; Yaroschak, M. M. Inhibitors of AKT activity. Inhibitors of AKT activity. PCT Int. Appl. WO 2010088177 A1 5 Aug 2010. Chem. Abstr. 2010, 153, 286970.Search in Google Scholar

Bakavoli, M.; Bagherzadeh, G.; Vaseghifar, M.; Shiri, A.; Pordel, M.; Mashreghi, M.; Pordeli, P.; Araghi, M. Molecular iodine promoted synthesis of new pyrazolo[3,4-d]pyrimidine derivatives as potential antibacterial agents. Eur. J. Med. Chem. 2010, 45, 647–650.10.1016/j.ejmech.2009.10.051Search in Google Scholar PubMed

Dinakaran, M.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. Antitubercular activities of novel benzothiazolo naphthyridone carboxylic acid derivatives endowed with high activity toward multi-drug resistant tuberculosis. Biomed. Pharmacother. 2009, 63, 11–18.10.1016/j.biopha.2007.10.009Search in Google Scholar PubMed

Dolle, R. E.; Bourdonnec, B. L.; Goodman, A. J.; Morales, G. A.; Thomas, C. J.; Zhang, W. Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2007. J. Comb. Chem. 2008, 10, 753–802.10.1021/cc800119zSearch in Google Scholar PubMed

Furuyama, H.; Goto, Y.; Kawanishi, N.; Layton, M. E.; Mita, T.; Naya, A.; Ogino, Y.; Onozaki, Y.; Rodzinak, K. J.; Sakamoto, T.; Sanderson, P. E.; Wang, J. B. Inhibitors of AKT activity. PCT Int. Appl. WO 2009148916 A1 10 Dec 2009. Chem. Abstr. 2009, 152, 57319.Search in Google Scholar

Huang, X. G.; Zhang, A. Q.; Chen, D. L.; Jia, Z. H.; Li, X. S. 4-Substituted 4-(1H-1,2,3-triazol-1-yl)piperidine: novel C7 moieties of fluoroquinolones as antibacterial agents. Bioorg. Med. Chem. Lett. 2010, 20, 2859–2863.10.1016/j.bmcl.2010.03.044Search in Google Scholar PubMed

Liéby, M. F.; Constantieux, T.; Jean, R. J. Multicomponent domino reaction from β-ketoamides: highly efficient access to original polyfunctionalized 2,6-diazabicyclo[2.2.2]octane cores. J. Am. Chem. Soc. 2005, 127, 17176–17177.10.1021/ja055885zSearch in Google Scholar PubMed

Lukka, P. B.; Paxton, J. W.; Kestell, P.; Baguley, B. C. Pharmacokinetics and distribution of SN 28049, a novel DNA binding anticancer agent, in mice. Cancer Chemother. Pharmacol. 2010, 65, 1145–1152.10.1007/s00280-009-1123-5Search in Google Scholar PubMed

Ramesh, D.; Chary, M. T.; Laxminarayana, E.; Sreenivasulu, B. Synthesis and antimicrobial activity of 1-alkyl and aryl-3-(2-methyl-1,8-naphthyridin-3-yl)ureas. Indian J. Chem. B 2010, 49B, 1271–1273.10.1002/chin.201103166Search in Google Scholar

Roma, G.; Di Braccio, M.; Grossi, G.; Piras, D.; Ballabeni, V.; Tognolini, M.; Bertoni, S.; Barocelli, E. 1,8-Naphthyridines VIII. Novel 5-aminoimidazo[1,2-a] [1,8]naphthyridine-6-carboxamide and 5-amino[1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamide derivatives showing potent analgesic or anti-inflammatory activity, respectively, and completely devoid of acute gastrolesivity. Eur. J. Med. Chem. 2010, 45, 352–366.10.1016/j.ejmech.2009.10.020Search in Google Scholar PubMed

Sanderson, P. E.; Layton, M. E.; Rodzinak, K. J. Inhibitors of AKT activity. PCT Int. Appl. WO 2010104705 A1 16 Sep 2010. Chem. Abstr. 2010, 153, 398795.Search in Google Scholar

Srinivasu, V. N. V.; Rajashekar, B. L.; Srinivas, K. An efficient one-pot three-component synthesis of 4-phenylhexahydro-1H-pyrano[2,3-d]pyrimidin-2(8aH)-one derivatives. J. Heterocycl. Chem. 2010, 47, 687–690.Search in Google Scholar

Tietze, L. F. Domino reactions in organic synthesis. Chem. Rev. 1996, 96, 115–136.10.1021/cr950027eSearch in Google Scholar PubMed

Victorio, C.; José, G.; Noel, N. One-pot three-component synthesis of tetrasubstituted N-H pyrroles from secondary propargylic alcohols, 1,3-dicarbonyl compounds and tert-butyl carbamate. J. Heterocycl. Chem. 2010, 47, 233–236.10.1002/jhet.301Search in Google Scholar

Vijjay, N. C.; Rajesh, A. U.; Vinod, S.; Bindu, A. R.; Sreekanth, J. S.; Lakshmi, B. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. Acc. Chem. Res. 2003, 36, 899–907.10.1021/ar020258pSearch in Google Scholar PubMed

Wang, X. S.; Zhang, M. M.; Jiang, H.; Shi, D. Q.; Tu, S. J.; Wei, X. Y.; Zong, Z. M. An improved and benign synthesis of 9,10-diarylacridin-1,8-dione and indenoquinoline derivatives from 3-arylamino-5,5-dimethylcyclohex-2-enone, arylaldehyde and 1,3-dicarbonyl compound in ionic liquid medium. Synthesis 2006, 4187–4199.10.1055/s-2006-950365Search in Google Scholar

Wang, X. S.; Zhang, M. M.; Jiang, H.; Tu, S. J. Three-component green synthesis of N-arylquinoline derivatives in ionic liquid [Bmim][BF4]: reactions of arylaldehyde, 3-arylamino-5,5-dimethylcyclohex-2-enone, and active methylene compounds. Tetrahedron 2007, 63, 4439–4449.10.1016/j.tet.2007.03.068Search in Google Scholar

Wang, X. S.; Li, Q.; Yao, C. S.; Tu, S. J. An efficient method for the synthesis of benzo[f]quinoline and benzo[a]phenanthridine derivatives catalyzed by iodine by a three-component reaction of arenecarbaldehyde, naphthalen-2-amine, and cyclic ketone. Eur. J. Org. Chem. 2008, 3513–3518.10.1002/ejoc.200800287Search in Google Scholar

Wang, X. S.; Li Q.; Wu, J. R.; Tu, S. J. Efficient method for the synthesis of pyranoquinoline, thiopyranoquinoline, thienoquinoline, and naphtho[2,7]naphthyridine derivatives catalyzed by iodine. J. Comb. Chem. 2009, 11, 433–437.10.1021/cc900026xSearch in Google Scholar PubMed

Wang, X. S.; Yang, K.; Zhou, J.; Tu, S. J. Facile method for the combinatorial synthesis of 2,2-disubstituted quinazolin-4(1H)-one derivatives catalyzed by iodine in ionic liquids. J. Comb. Chem. 2010, 12, 417–421.10.1021/cc900174pSearch in Google Scholar PubMed

Wang, W.; Lu, L.; Wang, X. S. An efficient method for the synthesis of naphthoquinoline derivatives catalyzed by iodine. Heterocycl. Commun. 2012, 18, 17–21.10.1515/hc-2011-0059Search in Google Scholar

Received: 2004-03-19
Accepted: 2004-06-04
Published Online: 2012-08-01
Published in Print: 2012-08-01

©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston

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