Abstract
An efficient and convenient method for synthesis of dihydropyrano[3,2-c]chromene derivatives by one-pot, three-component reaction of aldehydes, malononitrile, and 4-hydroxycoumarin in the presence of a catalytic amount of hexamethylenetetramine is reported. A variety of dihydropyrano[3,2-c]chromene derivatives were obtained in high to excellent yields within short times.
Graphical abstract
Similar content being viewed by others
References
Musa MA, Cooperwood JS, Khan MOF (2008) Curr Med Chem 15:2664
Kumar A, Maurya RA, Sharma SA, Ahmad P, Singh AB, Bhatia G, Srivastava AK (2009) Bioorg Med Chem Lett 19:6447
Raj T, Bhatia RK, Kapur A, Sharma M, Saxena AK, Ishar MPS (2010) Eur J Med Chem 45:790
Abdelrazek FM, Metz P, Farrag EK (2004) Arch Pharm 337:482
Symeonidis T, Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE (2009) Eur J Med Chem 44:5012
Raj T, Bhatia RK, Sharma RK, Gupta V, Sharma D, Ishara MPS (2009) Eur J Med Chem 44:3209
Gong K, Wang HL, Luo J, Liu ZL (2009) J Heterocycl Chem 46:1145
Huang CN, Kuo PY, Lin CH, Yang DY (2007) Tetrahedron 63:10025
Lin CC, Hsieh CC, Yu YC, Lai CH, Huang CN, Kuo PY, Lin CH, Yang DY, Chou PT (2009) J Phys Chem A 113:9321
Rueping M, Sugiono E, Merino E (2008) Chem Eur J 14:6329
Lacova M, Gasparova R, Kois P, Bohac A, El-Shaaer HM (2010) Tetrahedron 66:1410
Lacova M, Stankovicova H, Bohac A, Kotzianova B (2008) Tetrahedron 64:9646
El-Agrody AM, El-Latif MSA, El-Hady NA, Fakery AH, Bedair AH (2001) Molecules 6:519
Shaker RM (1996) Pharmazie 51:148
El-Agrody AM, Abd El-Latif MS, Fakery AH, Bedair AH (2000) J Chem Res 26
Wang J, Shi DQ, Zhuang QY, Wang XS, Hu HW (2004) J Chem Res 818
Shi DQ, Wu N, Zhuang QY (2008) J Chem Res 542
Al-Mousawi SM, Elkholy YM, Mohammad MA, Elnagdi MH (1999) Org Prep Proced Int 31:305
Anary-Abbasinejad M, Anaraki-Ardakani H, Ghanea F (2009) Monatsh Chem 140:397
Bayat M, Imanieh H, Shiraz NZ, Qavidel MS (2010) Monatsh Chem 141:333
Davoodnia A, Heravi MM, Rezaei-Daghigh L, Tavakoli-Hoseini N (2009) Monatsh Chem 140:149
Shaabani A, Rezazadeh F, Soleimani E (2008) Monatsh Chem 139:931
Teimouri MB, Bazhrang R (2009) Monatsh Chem 140:513
Heravi MM, Jani BA, Derikvand F, Bamoharram FF, Oskooie HA (2008) Catal Commun 10:272
Heravi MM, Sadjadi S, Haj NM, Oskooie HA, Bamoharram FF (2009) Catal Commun 10:1643
Shaabani A, Samadi S, Badri Z, Rahmati A (2005) Catal Lett 104:39
Seifi M, Sheibani H (2008) Catal Lett 126:275
Abdolmohammadi S, Balalaie S (2007) Tetrahedron Lett 48:3299
Khurana JM, Kumar S (2009) Tetrahedron Lett 50:4125
Wang XS, Zeng ZS, Shi DQ, Wei XY, Zong ZM (2005) Chin J Org Chem 25:1138
Shi DQ, Wang J, Zhuang QY, Wang XS (2006) Chin J Org Chem 26:643
de Souza R, Meireles BA, Aguiar CS, Vasconcellos M (2004) Synthesis 1595
Ribeiro RS, de Souza R, Vasconcellos M, Oliveira BL, Ferreira LC, Aguiar LCS (2007) Synthesis 61
Naeimi H (2008) J Chin Chem Soc 55:1156
Zhang ZH, Wang HJ, Ren XQ, Zhang YY (2009) Monatsh Chem 140:1481
Zhang P, Zhang ZH (2009) Monatsh Chem 140:199
Zhang Z-H, Tao X-Y (2008) Aust J Chem 61:77
Liu Y-H, Zhang Z-H, Li T-S (2008) Synthesis 3314
Liu Y-H, Liu Q-S, Zhang Z-H (2009) Tetrahedron Lett 50:916
Liu Y-H, Liu Q-S, Zhang Z-H (2008) J Mol Catal A Chem 296:42
Abd-El-Aziz AS, El-Agrody AM, Bedair AH, Corkery TC, Ata A (2004) Heterocycles 63:1793
Mostafa MS (2008) J Environ Sci 36:255
Acknowledgments
We thank the National Natural Science Foundation of China (20872025), the Nature Science Foundation of Hebei Province (B2008000149), and the Research Foundation for the Graduate Program of Hebei Normal University for financial support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wang, HJ., Lu, J. & Zhang, ZH. Highly efficient three-component, one-pot synthesis of dihydropyrano[3,2-c]chromene derivatives. Monatsh Chem 141, 1107–1112 (2010). https://doi.org/10.1007/s00706-010-0383-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-010-0383-4