Abstract
Various 4H-benzo[b]pyran derivatives were synthesized via a one-pot three-component condensation of arylaldehyde, malononitrile and dimedone in water using β-cyclodextrin (β-CD) as an efficient catalyst. This method provides several advantages, including mild reaction conditions, operational simplicity, high yields and minimal pollution of the environment.
Similar content being viewed by others
References
W.O. Foye, Prinicipi di Chemico Farmaceutica (Padova, Piccin, 1991), p. 416
L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517–520 (1993)
K. Singh, J. Singh, H. Singh, Tetrahedron 52, 14273–14280 (1996)
J. Skommer, D. Wlodkowic, M. Mvttc, M. Eray, J. Pelkonen, Leukemia Res. 30, 322–331 (2006)
D.R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W.F. Vernier, L. Lee, S. Liu, A. Sambandam, P.A. Snider, L. Masih, Bioorg. Med. Chem. Lett. 15, 1587–1590 (2005)
S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc., Chem. Commun. 17, 1202–1204 (1988)
R. Gonzalez, N. Martin, C. Seoane, J.L. Marco, A. Albert, F.H. Cano, Tetrahedron Lett. 33, 3809–3812 (1992)
D. Armesto, W.M. Horspool, N. Martin, A. Ramos, C. Seaone, J. Org. Chem. 54, 3069–3072 (1989)
D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu, H.W. Hu, Chin. J. Org. Chem. 23, 877–879 (2003)
L.M. Wang, J.H. Shao, H.Y. Tian, H. Wang, B. Liu, J. Fluorine Chem. 127, 97–100 (2006)
S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron 64, 9143–9149 (2008)
S. Balalaie, M.S. Ahmadi, M. Bararjaniom, Catal. Commun. 8, 1724–1728 (2007)
G. Sabitha, K. Arundhathi, K. Sundhakar, B.S. Sastry, J.S. Yadav, Synth. Commun. 39, 433–442 (2009)
R. Hekmatashoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307–310 (2008)
N. Sara, B. Raouf, C. Bertrand, D. Abdelmadjid, C. R. Chimie 15, 394–398 (2012)
T. Daryoush, A.B. Jessica, I.B. Sophia, Synth. Commun. 41, 2701–2711 (2011)
S.S. Katkar, M.K. Lande, B.R. Arbad, S.T. Gaikwad, Chin. J. Chem. 29, 199–202 (2011)
K. Tabatabaeian, H. Heidari, M. Mamaghani, N.O. Mahmoodi, Appl. Organometal. Chem. 26, 56–61 (2012)
I.A. Azath, P. Puthiaraj, K. Pitchumani, ACS Sustain. Chem. Eng. 1, 174–179 (2013)
Z. Fan, C.H. Diao, H.B. Song, Z.L. Jing, M. Yu, X. Chen, M.J. Guo, J. Org. Chem. 71, 1244–1246 (2006)
K. Uekama, F. Hirayama, I. Irie, Chem. Rev. 98, 2045–2076 (1998)
M. Narender, M.S. Reddy, R. Sridhar, Y.V.D. Nageswar, K.R. Rao, Tetrahedron Lett. 46, 5953–5955 (2005)
V.P. Rao, N.J. Turro, V. Ramamurthy, Tetrahedron Lett. 30, 4641–4644 (1989)
M.S. Moustafa, S.M. Al-Mousawi, M.A. Selim, A.M. Mosallam, M.H. Elnagdi, Beilstein J. Org. Chem. 10, 141–149 (2014)
Acknowledgments
The work was supported by funds from the National Natural Science Foundation of China: 21442012 and the Chinese Academy of Sciences.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lu, J., Fu, Xw., Zhang, G. et al. β-Cyclodextrin as an efficient catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in water. Res Chem Intermed 42, 417–424 (2016). https://doi.org/10.1007/s11164-015-2027-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2027-0