Under the action of an excess of trifluoromethanesulfonic acid, 1-aryl-5-phenylpent-4-en-2-yn-1-ones cyclize intramolecularly to 6-aryl-2-phenyl-2,3-dihydropyran-4-ones. The reaction proceeds at room temperature for 1 h with 50–60% yields.
Similar content being viewed by others
References
Golovanov, A. A.; Odin, I. S.; Zlotski, S. S. Russ. Chem. Rev. 2019, 88, 280. [Usp. Khim. 2019, 88, 280.]
Golovanov, A. A.; Gusev, D. M.; Zlotskii, S. S. Russ. J. Org. Chem. 2016, 52, 1205. [Zh. Org. Khim. 2016, 52, 1212.]
Dhiman, S.; Ramasastry, S. S. V. Org. Lett. 2015, 17, 5116.
Mokar, B. D.; Liu, R.-S. Chem. Commun. 2014, 50, 8966.
Meng, F.-F.; Xie, J.-H.; Xu, Y.-H.; Loh, T.-P. ACS Catal. 2018, 8, 5306.
Mondal, A.; Hazra, R.; Grover, K.; Raghu, M.; Ramasastry, S. S. V. ACS Catal. 2018, 8, 2748.
Saulnier, S.; Lozovskiy, S. V.; Golovanov, A. A.; Ivanov, A. Yu.; Vasilyev, A. V. Eur. J. Org. Chem. 2017, 3635.
Olah, G. A.; Prakash, G. K. S.; Sommer, J.; Molnar, A. Superacid Chemistry; Wiley: New York, 2009, p. 525.
MacDonald, F. K.; Burnall, D. J. J. Org. Chem. 2009, 74, 6973.
Yang, F.; Ji, K.-G.; Zhao, S.-C.; Ali, S.; Ye, Y.-Y.; Liu, X.-Y.; Liang, Y.-M. Chem.–Eur. J. 2012, 18, 6470.
Zheng, J.; Lin, L.; Fu, K.; Zhang, Y.; Liu, X.; Feng, X. Chem.– Eur. J. 2014, 20, 14493.
Larrosa, I.; Romea, P.; Urpi, F. Tetrahedron 2008, 64, 2683.
Clarke, P. A.; Santos, S. Eur. J. Org. Chem. 2006, 2045.
Michaelides, I. N.; Darses, B.; Dixon, D. J. Org. Lett. 2011, 13, 664.
Torrado, A.; Lopez, S.; Alvarez, R.; de Lera, A. R. Synthesis 1995, 285.
Hoshi, M.; Yamazaki, H.; Okimoto, M. Synlett 2010, 2461.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 953–956
Electronic supplementary material
ESM1
(PDF 4842 kb)
Rights and permissions
About this article
Cite this article
Zalivatskaya, A.S., Golovanov, A.А. & Vasilyev, A.V. Cyclization of 1-Aryl-5-Phenylpent-4-en-2-yn-1-Ones to 2,3-Dihydropyran-2-Ones in Trifluoromethanesulfonic Acid. Chem Heterocycl Comp 56, 953–956 (2020). https://doi.org/10.1007/s10593-020-02756-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02756-8