A facile synthesis of 2-aryl-4-(indol-3-yl)-4H-chromenes using amberlyst-15 as an efficient recyclable heterogeneous catalyst
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Abstract
Starting from 2-hydroxychalcones and indoles, a facile synthesis of 2-aryl-4-(indol-3-yl)-4H-chromenes has been achieved by use of amberlyst-15, a sulfonated polystyrene resin, as a recyclable heterogeneous catalyst. The methodology involves a domino sequence of Michael addition, cyclization, and dehydration.
Graphical abstract
Keywords
2-Aryl-4-(indol-3-yl)-4H-chromenes Heterogeneous catalysis Michael addition CyclizationNotes
Acknowledgments
Financial assistance from the UGC-CAS and DST-PURSE programs, Department of Chemistry is gratefully acknowledged. The authors also acknowledge the DST-FIST program to the Department of Chemistry, Jadavpur University for providing the NMR spectral data. CG and NS are thankful to the UGC, New Delhi for their Research Fellowships.
Supplementary material
References
- 1.Iacobucci GA, Sweeny JG (1983) Tetrahedron 39:3005CrossRefGoogle Scholar
- 2.Shestopalov AM, Litvinov YM, Rodinovskaya LA, Malyshev OR, Semenova MN, Semenov VV (2012) ACS Comb Sci 14:484CrossRefGoogle Scholar
- 3.Tripathi AK, Mukherjee D, Koul S, Taneja SC, Agrawal SK, Sharma PR, Saxena AK (2011) Ind J Chem 50B:1619Google Scholar
- 4.Kidwai M, Saxena S, Khan MKR, Thukral SS (2005) Bioorg Med Chem Lett 15:4295CrossRefGoogle Scholar
- 5.Kemnitzer W, Drewe J, Jiang S, Zhang H, Zhao J, Crogan-Grundy C, Xu L, Lamothe S, Gourdeau H, Denis R, Tseng B, Kasibhatla S, Cai SX (2007) J Med Chem 50:2858CrossRefGoogle Scholar
- 6.Kemnitzer W, Drewe J, Jiang S, Zhang H, Crogan-Grundy C, Denis L, Bubenick M, Attardo G, Denis R, Lamothe S, Gourdeau H, Tseng B, Shailaja K, Cai SX (2008) J Med Chem 51:417CrossRefGoogle Scholar
- 7.Gadwood RC, Kamdar BV, Dubray LAC, Wolfe ML, Smith MP, Watt W, Mizsak SA, Groppit VE (1993) J Med Chem 36:1480CrossRefGoogle Scholar
- 8.Towers GHN, Rodriguez E (1983) J Nat Prod 46:331CrossRefGoogle Scholar
- 9.Meepagala KM, Osbrink W, Burandt C, Laxb A, Dukea SO (2011) Pest Manag Sci 67:1446CrossRefGoogle Scholar
- 10.Hobley J, Malatesta V, Millini R, Giroldini W, Wis L, Goto M, Kishimoto M, Fukumura H (2000) Chem Commun 36:1339Google Scholar
- 11.Zhang X, Zhang S, Wang W (2010) Angew Chem Int Ed 49:1481CrossRefGoogle Scholar
- 12.Yang G, Luo C, Mu X, Wang T, Liu XY (2012) Chem Commun 48:5880CrossRefGoogle Scholar
- 13.Bello D, Ruiz-Rodríguez J, Albericio F, Ramón R, Lavilla R (2010) Eur J Org Chem 28:5373CrossRefGoogle Scholar
- 14.Kharrat SE, Laurent P, Blancou H (2006) J Org Chem 71:8637CrossRefGoogle Scholar
- 15.Liu Y, Qian J, Lou S, Zhu J, Xu Z (2010) J Org Chem 75:1309CrossRefGoogle Scholar
- 16.Shi YL, Shi M (2007) Org Biomol Chem 5:1499CrossRefGoogle Scholar
- 17.Malakar CC, Schmidt D, Conrad J, Beifuss U (2011) Org Lett 13:1972CrossRefGoogle Scholar
- 18.Sharma V, Kumar P, Pathak D (2010) J Heterocycl Chem 47:491Google Scholar
- 19.Lamotte Y, Martres P, Faucher N, Laroze A, Grillot D, Ancellin N, Saintillan Y, Beneton V, Gampe RT (2010) Bioorg Med Chem Lett 20:1399CrossRefGoogle Scholar
- 20.Kitano M, Kojima A, Nakano K, Miyagishi A, Noguchi T, Ohashi N (1999) Chem Pharm Bull 47:1538CrossRefGoogle Scholar
- 21.Shanthi G, Perumal PT (2007) Tetrahedron Lett 48:6785CrossRefGoogle Scholar
- 22.Chen W, Cal Y, Fu X, Liu X, Lin L, Feng X (2011) Org Lett 13:4910CrossRefGoogle Scholar
- 23.Pang W, Han JW, Zhao JW, Zhu SZ (2011) Synthesis 2011:3364Google Scholar
- 24.Yin G, Fan L, Ren T, Zheng C, Tao Q, Wub A, She N (2012) Org Biomol Chem 10:8877CrossRefGoogle Scholar
- 25.Guha C, Mondal R, Pal R, Mallik AK (2013) J Chem Sci 125:1463CrossRefGoogle Scholar
- 26.Jackson AH, Smith AE (1965) Tetrahedron 21:989 and references cited thereinGoogle Scholar
- 27.Pal R, Sarkar T, Khasnobis S (2012) Arkivoc (i):570Google Scholar
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