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
Similar content being viewed by others
References
Iacobucci GA, Sweeny JG (1983) Tetrahedron 39:3005
Shestopalov AM, Litvinov YM, Rodinovskaya LA, Malyshev OR, Semenova MN, Semenov VV (2012) ACS Comb Sci 14:484
Tripathi AK, Mukherjee D, Koul S, Taneja SC, Agrawal SK, Sharma PR, Saxena AK (2011) Ind J Chem 50B:1619
Kidwai M, Saxena S, Khan MKR, Thukral SS (2005) Bioorg Med Chem Lett 15:4295
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 50:2858
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 51:417
Gadwood RC, Kamdar BV, Dubray LAC, Wolfe ML, Smith MP, Watt W, Mizsak SA, Groppit VE (1993) J Med Chem 36:1480
Towers GHN, Rodriguez E (1983) J Nat Prod 46:331
Meepagala KM, Osbrink W, Burandt C, Laxb A, Dukea SO (2011) Pest Manag Sci 67:1446
Hobley J, Malatesta V, Millini R, Giroldini W, Wis L, Goto M, Kishimoto M, Fukumura H (2000) Chem Commun 36:1339
Zhang X, Zhang S, Wang W (2010) Angew Chem Int Ed 49:1481
Yang G, Luo C, Mu X, Wang T, Liu XY (2012) Chem Commun 48:5880
Bello D, Ruiz-Rodríguez J, Albericio F, Ramón R, Lavilla R (2010) Eur J Org Chem 28:5373
Kharrat SE, Laurent P, Blancou H (2006) J Org Chem 71:8637
Liu Y, Qian J, Lou S, Zhu J, Xu Z (2010) J Org Chem 75:1309
Shi YL, Shi M (2007) Org Biomol Chem 5:1499
Malakar CC, Schmidt D, Conrad J, Beifuss U (2011) Org Lett 13:1972
Sharma V, Kumar P, Pathak D (2010) J Heterocycl Chem 47:491
Lamotte Y, Martres P, Faucher N, Laroze A, Grillot D, Ancellin N, Saintillan Y, Beneton V, Gampe RT (2010) Bioorg Med Chem Lett 20:1399
Kitano M, Kojima A, Nakano K, Miyagishi A, Noguchi T, Ohashi N (1999) Chem Pharm Bull 47:1538
Shanthi G, Perumal PT (2007) Tetrahedron Lett 48:6785
Chen W, Cal Y, Fu X, Liu X, Lin L, Feng X (2011) Org Lett 13:4910
Pang W, Han JW, Zhao JW, Zhu SZ (2011) Synthesis 2011:3364
Yin G, Fan L, Ren T, Zheng C, Tao Q, Wub A, She N (2012) Org Biomol Chem 10:8877
Guha C, Mondal R, Pal R, Mallik AK (2013) J Chem Sci 125:1463
Jackson AH, Smith AE (1965) Tetrahedron 21:989 and references cited therein
Pal R, Sarkar T, Khasnobis S (2012) Arkivoc (i):570
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.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Guha, C., Sepay, N. & Mallik, A.K. A facile synthesis of 2-aryl-4-(indol-3-yl)-4H-chromenes using amberlyst-15 as an efficient recyclable heterogeneous catalyst. Monatsh Chem 146, 1349–1354 (2015). https://doi.org/10.1007/s00706-014-1401-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-014-1401-8