Abstract
An environmentally benign novel strategy is developed for the synthesis of tetrahydrobenzo[b]pyrans by using thiamine mononitrate as a green catalyst, with the help of a conventional as well as non-conventional energy source. Synthesis of tetrahydrobenzo[b]pyrans is achieved by one pot condensation of aromatic aldehydes, malononitrile and dimedone in a water–ethanol system. Use of aqueous reaction media, mild conditions, water stable catalyst and energy plummeting process as well as excellent yield, are the key features in completing the reaction. This method excludes the use of volatile organic solvents, tedious workup and column chromatographic purification of compounds, making the method greener, convenient and superior.
Graphical Abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
A. DomLing, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)
R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16, 2958 (2014)
G. Pandey, R.P. Singh, A. Gary, V.K. Singh, Tetrahedron Lett. 46, 2137 (2005)
D. Rajguru, B.S. Keshwal, S. Jain, Med. Chem. Res. (2013). doi:10.1007/s00044-013-0586-4
S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem Soc. Chem Commun. 17, 1202 (1988)
N. Hazeri, M.T. Maghsoodlou, M.R. Mousavi, J. Aboonajmi, M. Safarzaei, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1179-z
P.L. Anandgaonker, S. Jadhav, S.T. Gaikwad, A.S. Rajbhoj, J. Clust. Sci. 25, 483 (2014)
F. Khorami, H.R. Shaterian, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1423-6
A. Sánchez, F. Hernández, P.C. Cruz, Y. Alcaraz, J. Tamariz, F. Delgado, M.A. Vázquez, J. Mex. Chem. Soc. 56(2), 121 (2012)
N.S. Fatemeh, T.M. Malek, H. Nourallah, K. Mehrnoosh, Res. Chem. Intermed. 41(8) (2015). doi:10.1007/s11164-014-1710-x
S.B. Lalaie, M. Bararjanian, A.M. Amani, B. Movassagh, SYNLETT, 2, 0263 (2006)
Y. Li, H. Chen, C. Shi, S. Ji, J. Comb. Chem. 12, 231 (2010)
N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35, 391 (2014)
T.S. Jin, A.Q. Wang, F. Shi, L.S. Han, L.B. Liu, T.S. Li, ARKIVOC, xiv, 78 (2006)
M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)
R. Pagadala, S. Maddila, S.B. Jonnalagadda, J. Heterocycl. Chem. (2015). doi:10.1002/jhet.2125
J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)
W.O. Sun, P. Zhang, J. Fan, S.H. Chen, Z.H. Zhang, Synth. Commun. 40, 587 (2010)
D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 47, 63 (2010)
R.S. Bhosale, S.R. Sarda, S. Ardhapure, W.N. Jadhav, S.R. Bhusareb, R.P. Pawar, Tetrahedron Lett. 46, 7183 (2005)
S. Fatma, D. Singh, P. Ankit, P. Mishra, M. Singh, J. Singh, Tetrahedron Lett. 55, 2201–2207 (2014)
M. Lei, L. Maa, L. Hu, Tetrahedron Lett. 51, 4186–4188 (2010)
P.V. Badadhe, A.V. Chate, D.G. Hingane, P.S. Mahajan, N.M. Chavhan, C.H. Gill, J. Korean Chem. Soc. 55 (2011)
M. Lei, L. Ma, L. Hu, Synthetic Commun. 41, 1969–1976 (2011)
F. Chen, M. Lei, L. Hu, Tetrahedron 69, 2954–2960 (2013)
I.R. Siddiqui, P. Rai, A. Srivastava, A. Srivastava, A. Srivastava, New J. Chem. (2013). doi:10.1039/c3nj00711a
H. Dugas, C. Penney, Bioorganic Chemistry: A Chemical Approach to Enzyme Action (Springer, New York, 1981). doi:10.1007/978-1-4684-0095-3
Acknowledgments
We are thankful to Dr. R. S. Agrawal, Principal J.E.S. College Jalna, for providing laboratory facilities and kind support in the completion of this work.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Khandebharad, A.U., Sarda, S.R., Gill, C.H. et al. Condition based divergence in synthesis of tetrahydrobenzo[b]pyrans. Res Chem Intermed 42, 5779–5787 (2016). https://doi.org/10.1007/s11164-015-2403-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2403-9