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Synthesis 2014; 46(13): 1807-1814
DOI: 10.1055/s-0033-1341027
DOI: 10.1055/s-0033-1341027
paper
Molecular Iodine Mediated Regioselective Synthesis of Pyranocoumarins and Bis-Fused Benzo-2H-pyran Derivatives
Further Information
Publication History
Received: 08 January 2014
Accepted after revision: 25 February 2014
Publication Date:
07 April 2014 (online)
Abstract
A simple and straightforward approach for the regioselective synthesis of pyranocoumarin and bis-fused benzo-2H-pyran derivatives using mild, easy to handle, and cheaper molecular iodine mediated heterocyclization is described.
Key words
molecular iodine - 6-endo-dig - electrophilic cylization - bis-fused benzo-2H-pyrans - pyranocoumarinsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Present address: Department of Chemistry, The University of Burdwan, Burdwan, W. B., India.
- 2a Wang GX, Wang NX, Shi T, Yu JL, Tang XL. Prog. Chem. 2008; 20: 518
- 2b Zhendong J, Ying K. PCT Int Appl WO 2004058738, 2004
- 2c Iwata N, Wang N, Yao X, Kitanaka S. J. Nat. Prod. 2004; 67: 1106
- 2d Hu H, Harrison TJ, Wilson PD. J. Org. Chem. 2004; 69: 3782
- 2e Mun J, Jabbar AA, Devi NS, Yin S, Wang Y, Tan C, Culver D, Snyder JP, Van Meir EG, Goodman MM. J. Med. Chem. 2012; 55: 6738
- 2f Harel D, Schepmann D, Prinz H, Brun R, Schmidt TJ, Wunsch B. J. Med. Chem. 2013; 56: 7442
- 2g Bonadies F, Di Fabio R, Bonini C. J. Org. Chem. 1984; 49: 1647
- 2h Morandim AA, Bergamo DC. B, Kato MJ, Cavalheiro AJ, Bolzani VS, Furlan M. Phytochem. Anal. 2005; 16: 282
- 3 Kwak JH, Kang HE, Jung JK, Kim H, Cho J, Lee H. Arch. Pharm. Res. 2006; 29: 934
- 4 Emami S, Kebriaeezadeh A, Zamani MJ, Shafiee A. Bioorg. Med. Chem. Lett. 2006; 16: 1803
- 5 Kanbe Y, Kim MH, Nishimoto M, Ohtake Y, Kato N, Tsunenari T, Taniguchi K, Ohizumi I, Kaiho S, Morikawa K, Jo JC, Lim HS, Kim HY. Bioorg. Med. Chem. 2006; 14: 4803
- 6 Koufaki M, Kiziridi C, Alexi X, Alexis MN. Bioorg. Med. Chem. 2009; 17: 6432
- 7a Torrejón GC, Kahn SA, Lagarde N, Castellano F, Leblanc K, Rodrigo J, Frenkel VM, de Arias AR, Ferreira ME, Thirant C, Fournet A, Figadère B, Chneiweiss H, Poupon E. J. Nat. Prod. 2012; 75: 257
- 7b Krohn K, Sohrab MdH, van Ree T, Draeger S, Schulz B, Antus S, Kurtan T. Eur. J. Org. Chem. 2008; 5638
- 7c Stewart AM, Meier K, Schulz B, Steinert M, Snider BB. J. Org. Chem. 2010; 75: 6057
- 7d Ma T, Liu L, Xue H, Li L, Han C, Wang L, Chen Z, Liu G. J. Med. Chem. 2008; 51: 1432
- 7e Kang H.-S, Kim K.-R, Jun E.-M, Park S.-H, Lee T.-S, Suh J.-W, Kim J.-P. Bioorg. Med. Chem. Lett. 2008; 18: 4047
- 7f Mo S, Wang S, Zhou G, Yang Y, Li Y, Chen X, Shi J. J. Nat. Prod. 2004; 67: 823
- 7g Jung EJ, Park BH, Lee YR. Green Chem. 2010; 12: 2003
- 8a Mali RS, Joshi PP, Sandhu PK, Manekar-Tilve A. J. Chem. Soc., Perkin Trans. 1 2002; 371
- 8b Shen Y.-C, Wang L.-T, Chen C.-Y. Tetrahedron Lett. 2004; 45: 187
- 8c Fong W.-F, Shen X.-L, Globisch C, Wiese M, Chen G.-Y, Zhu G.-Y, Yu Z.-L, Tse AK.-W, Hu Y.-J. Bioorg. Med. Chem. 2008; 16: 3694
- 8d Xie L, Takeuchi Y, Cosentino LM, McPhail AT, Lee K.-H. J. Med. Chem. 2001; 44: 664
- 8e Su C.-R, Yeh S.-F, Liu CM, Damu AG, Kuo T.-H, Chiang P.-C, Bastow KF, Lee K.-H, Wu T.-S. Bioorg. Med. Chem. 2009; 17: 6137
- 8f Nicolaides DN, Gautam DR, Litinas KE, Hadjipavlou-Litina DJ, Fylaktakidou KC. Eur. J. Med. Chem. 2004; 39: 323
- 9a Stefan B, Larsson LG, Rényi L, Ross SB, Thorberg S.-O, Thorell-Svantesson G. J. Med. Chem. 1998; 41: 1934
- 9b Ishizuka N, Matsumura K, Sakai K, Fujimoto M, Mihara S, Yamamori T. J. Med. Chem. 2002; 45: 2041
-
10a Menon RS, Findlay AD, Bissember AC, Banwell MG. J. Org. Chem. 2009; 74: 8901
- 10b Majumdar KC, Chakravorty S, De N. Tetrahedron Lett. 2008; 49: 3419
- 10c Majumdar KC, Mondal S. Tetrahedron Lett. 2009; 50: 4781
- 10d Barluenga J, Trincado M, Marco-Arias M, Ballesteros A, Rubio E, Gonzalez JM. Chem. Commun. 2005; 2008
- 11a Liu Y, Zhu J, Qian J, Jiang B, Xu Z. J. Org. Chem. 2011; 76: 9096
- 11b Appendino G, Cravotto G, Giovenzana GB, Palmisano G. J. Nat. Prod. 1999; 62: 1627
- 11c Sagar R, Park J, Koh M, Park SB. J. Org. Chem. 2009; 74: 2171
- 12a Fischer D, Tomeba H, Pahadi NK, Patil NT, Yamamoto Y. Angew. Chem. Int. Ed. 2007; 46: 4764
- 12b Yue D, Yao T, Larock RC. J. Org. Chem. 2006; 71: 62
- 12c Yue D, Larock RC. J. Org. Chem. 2002; 67: 1905
- 12d He Z, Li H, Li Z. J. Org. Chem. 2010; 75: 4636
- 12e Banwell MG, Wills AC, Hamel E. Aust. J. Chem. 1999; 52: 767
- 12f Flynn BL, Verdier-Pinard P, Hamel E. Org. Lett. 2001; 3: 651
- 12g Larock RC, Yue D. Tetrahedron Lett. 2001; 42: 6011
- 12h Hessian KO, Flynn BL. Org. Lett. 2003; 5: 4377
- 12i Kesharwani T, Worlikar SA, Larock RC. J. Org. Chem. 2006; 71: 2307
- 12j Sniady A, Wheeler KA, Dembinski R. Org. Lett. 2005; 7: 1769
- 12k Yao T, Zhang X, Larock RC. J. Org. Chem. 2005; 70: 7679
- 12l Xie Y.-X, Liu X.-Y, Wu L.-Y, Han Y, Zhao L.-B, Fan M.-J, Liang Y.-M. Eur. J. Org. Chem. 2008; 1013
- 13a Barluenga J, Trincado M, Rublio E, Gonzalez JM. Angew. Chem. Int. Ed. 2003; 42: 2406
- 13b Amjad M, Knight DW. Tetrahedron Lett. 2004; 45: 539
- 13c Yue D, Larock RC. Org. Lett. 2004; 6: 1037
- 13d Barluenga J, Vazque-Villa H, Ballesteros A, Gonzalez JM. J. Am. Chem. Soc. 2003; 125: 9028
- 13e Yue D, Della Ca N, Larock RC. Org. Lett. 2004; 6: 1581
- 13f Majumdar KC, Ray K, Ponra S. Tetrahedron Lett. 2010; 51: 5437
- 13g Majumdar KC, Sinha B, Ansary I, Chakravorty S. Synlett 2010; 1407
- 13h Majumdar KC, Ansary I, Sinha B, Roy B, Sridhar B. Synthesis 2011; 3287
- 14a Worlikar SA, Kesharwani T, Yao T, Larock RC. J. Org. Chem. 2007; 72: 1347
- 14b Masters K.-S, Flynn BL. J. Org. Chem. 2008; 73: 8081
-
14c Godoi B, Speranc A, Back DF, Brandao R, Nogueira CW, Zeni G. J. Org. Chem. 2009; 74: 3469
- 15 CCDC-809664 contains the supplementary crystallographic data of the compound 17a. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.