Abstract
The 2,4,6-trisubstituted pyridines constitute an important family of heterocyclic compounds widely used in industry, especially in pharmaceuticals, making their preparation a crucial challenge for organic chemists. In continuation of our approach in the preparation and development of new catalytic systems, we present in this paper a highly efficient one-step synthesis of triarylpyridine by Al/Ag3PO4 phosphate bimetallic catalysis from the condensation of acetophenone derivatives, aryl aldehydes, and ammonium acetate under mild and environmentally friendly conditions. This methodology offers several advantages: excellent yields and shorter reaction times. In addition, the catalyst exhibited remarkable reusable activity. Compared to previous methods, our procedure allows a very flexible, more straightforward, faster, and more efficient preparation of substituted pyridines.
Graphical abstract
Similar content being viewed by others
Data availability
Data analyzed in this work were a re-analysis of existing data, which are openly available at locations cited in the reference section. Further documentation about data processing and analysis are available as supplementary data.
References
Joule J, Mills K, Smith GF (2020) Heterocyclic Chemistry, 3rd edn. CRC Press
Jones G, Abarca B (2010) Adv Heterocycl Chem 100:195
Tatsumi K, Fukushima M, Shirasaka T, Fujii S (1987) Jpn J Cancer Res 78:748
Milstein D (2010) Top Catal 53:915
Thapa P, Karki R, Yun M, Kadayat T, Lee E, Kwon H, Cho W, Kim N, Jeong B, Kwon Y, Lee E (2012) Eur J Med Chem 52:123
Sims G, O’Loughlin E, Crawford R (1989) Crit Rev Environ Control 19:309
Chavan V, Sonawane S, Shingare MS, Karale BK (2006) Chem Heterocycl Compd 42:625
Altaf A, Shahzad A, Gul Z, Rasool N, Badshah A, Lal B, Khan E (2015) J Drug Des Med Chem 1:1
Hill M (2010) Chem Eur J 16:12052
Baloutaki BA, Sayahi MH, Nikpassand M, Kefayati H (2020) Res Chem Intermed 46:1153
Moosavi-Zare A, Zolfigol M, Farahmand S, Zare A, Pourali A, Ayazi-Nasrabadi R (2013) Synlett 25:193
Tabrizian E, Amoozadeh A, Rahmani S, Imanifar E, Azhari S, Malmir M (2015) Chin Chem Lett 26:1278
Chen Y, Zhang T, Wang D, Zhou J, Zhang Y, Li Y (2017) J Chem Sci 129:421
Wu P, Zhang X, Chen B (2019) Tetrahedron Lett 60:1103
Zhang X, Wen H, Yang Q, Zhou R, Song J (2020) Inorg Chim Acta 507:119600
Roozifar M, Hazeri N, Faroughi Niya H (2021) J Heterocycl Chem 58:1117
El Hallaoui A, Chehab S, Malek B, Zimou O, Ghailane T, Boukhris S, Souizi A, Ghailane R (2019) ChemistrySelect 4:3062
El Hallaoui A, Chehab S, Ghailane T, Malek B, Zimou O, Boukhriss S, Souizi A, Ghailane R (2021) Polycycl Aromat Compd 41:2083
El Hallaoui A, Ghailane T, Chehab S, Merroun Y, Ghailane R, Boukhris S, Guedira T, Souizi A (2021) Mediterr J Chem 11:215
Nagarapu L, Aneesa Peddiraju R, Apuri S (2007) Catal Commun 8(12):1973–1976
Ding Y, Ma R, Hider R, Ma Y (2020) Asian J Org Chem 9:242
Heravi M, Bakhtiari K, Daroogheha Z, Bamoharram F (2007) Catal Commun 8:1991
Ren Y, Cai C (2009) Monatsh Chem 140:49
Maleki B, Azarifar D, Veisi H, Hojati SF, Salehabadi H, Yami R (2010) Chin Chem Lett 21:1346
Moosavi-Zare A, Zolfigol M, Rezanejad Z (2016) Can J Chem 94:626
Maleki A, Firouzi-Haji R (2018) Sci Rep 8:17303
Maleki A, Hajizadeh Z, Firouzi-Haji R (2018) Microporous Mesoporous Mater 259:46
Han J, Guo X, Liu Y, Fu Y, Yan R, Chen B (2017) Adv Synth Catal 359:2676
Gadekar S, Lande M (2018) Res Chem Intermed 44:3267
Zarnegar Z, Safari J, Borjian-Borujeni M (2015) Chem Heterocycl Compd 50:1683
Asressu K, Chan C, Wang C (2021) ACS Omega 6:7296
Kamble S, Shankarling G (2018) ChemistrySelect 3:10464
Li M, Wang T, Wang C (2020) ChemistrySelect 5:3600
Shaabani A, Borjian-Boroujeni M, Laeini MS (2016) RSC Adv 6:27706
Reza M, Shafiee M, Moloudi R, Ghashang M (2012) APCBEE Proc 1:221
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
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
El Hallaoui, A., Merroun, Y., Chehab, S. et al. One-pot synthesis of 2,4,6-triarylpyridines by cyclocondensation between aryl aldehyde, acetophenone derivative, and ammonium acetate using Al/Ag3PO4 as a new and green bimetallic catalyst. Monatsh Chem 154, 231–237 (2023). https://doi.org/10.1007/s00706-022-03023-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-022-03023-6