The reaction of diethyl ethynyl- and 2-phenylethynylphosphonates with pyridinium methylides generated in situ from phenacyl- and 2-ethoxy-2-oxoethylpyridinium salts by the action of a base was studied. As a result of the reaction, the corresponding diethyl indolizin-1-ylphosphonates were formed. In this case, diethyl ethynylphosphonate demonstrated higher reactivity and underwent a reaction at room temperature in the K2CO3–MeCN system, while reactions with 2-phenylethynylphosphonate proceeded at elevated temperatures and resulted in lower indolizine yields.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Sharma, V.; Kumar, V. Med. Chem. Res. 2014, 23, 3593.
Singh, G. S.; Mmatli, E. E. Eur. J. Med. Chem. 2011, 46, 5237.
Saucier, M. A.; Smith, C.; Kruse, N. A.; Hammer, N. I.; Delcamp, J. H. Molecules 2023, 28, 1287.
Gayton, J.; Autry, S. A.; Meador, W.; Parkin, S. R.; Hill, G. A., Jr.; Hammer, N. I.; Delcamp, J. H. J. Org. Chem. 2019, 84, 687.
Chatterjee, S.; Shaik, A. K.; Wijesinghe, K. H.; Ndaleh, D.; Dass, A.; Hammer, N. I.; Delcamp, J. H. J. Org. Chem. 2022, 87, 11319.
Yu, Y.; Yi, S.; Zhu, C.; Hu, W.; Gao, B.; Chen, Y.; Wu, W.; Jiang, H. Org. Lett. 2016, 18, 400.
Shimizu, G. K. H.; Vaidhyanathan, R.; Taylor, J. M. Chem. Soc. Rev. 2009, 38, 1430.
Goura, J.; Chandrasekhar, V. Chem. Rev. 2015, 115, 6854.
Bae, E.; Choi, W.; Park, J.; Shin, H. S.; Kim, S. B.; Lee, J. S. J. Phys. Chem. B 2004, 108, 14093.
Yu, Y.; Yue, Z.; Ding, L.-g.; Zhou, Y.; Cao, H. ChemistrySelect 2019, 4, 1117.
Tolmachev, A. A.; Yurchenko, A. A.; Kozlov, E. S.; Shulezhko, V. A.; Pinchuk, A. M. Heteroat. Chem. 1993, 4, 343.
Nechaev, I. V.; Cherkaev, G. V. J. Org. Chem. 2022, 87, 14137.
Aguado, J. E.; Cativiela, C.; Gimeno, M. C.; Jones, P. G.; Laguna, A.; Sarroca, C. Eur. J. Inorg. Chem. 2009, 216.
Zhang, C.; Zhang, H.; Zhang, L.; Wen, T. B.; He, X.; Xia, H. Organometallics 2013, 32, 3738.
Liu, H.; He, D.; Sun, Z.; He, W.; Han, J.; Chen, J.; Deng, H.; Shao, M.; Zhang, H.; Cao, W. Tetrahedron 2018, 74, 135.
Shen, Y.; Zhang, Y.; Jiang, G.-F. Synthesis 2002, 714.
Zhu, S.; Zhang, Y.; Li, P.; Bi, W.; Chen, X.; Zhao, Y. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 1.
Song, W.; Zheng, N.; Li, M.; Ullah, K.; Zheng, Y. Adv. Synth. Catal. 2018, 360, 2429.
Feng, Q.; Huang, H.; Sun, J. Org. Lett. 2021, 23, 2431.
Philippov, I.; Gatilov, Y.; Sonina, A.; Vorob'ev, A. Molecules 2022, 27, 7913.
Allgäuer, D. S.; Mayer, P.; Mayr, H. J. Am. Chem. Soc. 2013, 135, 15216.
Ghandi, M.; Jameà, A. H. Tetrahedron Lett. 2011, 52, 4005.
Cockburn, N.; Karimi, E.; Tam, W. J. Org. Chem. 2009, 74, 5762.
SAINT. Data Reduction and Frame Integration Program for the CCD Area-Detector System; Madison, 1997.
Sheldrick G. M. SADABS; Goettingen: Institute for Inorganic Chemistry, University of Goettingen, 1996.
Sheldrick, G. M. Acta. Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.
Sheldrick, G. M. Acta. Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(11/12), 786–792
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Filippov, I.R., Sonina, A.A. & Vorob’ev, A.Y. The synthesis of indolizin-1-ylphosphonates via the reaction of ethynylphosphonates with pyridinium methylides. Chem Heterocycl Comp 59, 786–792 (2023). https://doi.org/10.1007/s10593-024-03272-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-024-03272-9