Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis
DOI: 10.1055/a-2623-8823
DOI: 10.1055/a-2623-8823
Paper
Novel Synthesis of 3-Amino-2-pyrones and 3-Hydroxy-4-pyridones via Double Ring-Opening Reactions of 4-Pyrone Epoxides with Amines
Funding Information This work was financially supported by the Russian Science Foundation (Grant 22-73-10236, https://rscf.ru/project/22-73-10236/).
Abstract
The general method for the synthesis of 3-amino-2-pyrones based on the domino reaction of 4-pyrone epoxides with amines has been developed. The formation of the products includes selective Michael addition, double ring-opening, and facile deformylation. The nature of amine has a strong effect on the transformation governed by the cyclization of polycarbonyl intermediates. The reaction with aromatic amines is followed by a side dearoylation process to produce dihydropyrroles. The use of ammonium acetate as a nucleophile in DMSO provides a new reaction pathway yielding 3-hydroxy-4-pyridones. Tautomerism of the obtained products has been studied.
Keywords
4-Pyrone epoxide - 3-Amino-2-pyrone - 3-Hydroxy-4-pyridone - Double ring-opening - DeformylationPublication History
Received: 16 March 2025
Accepted after revision: 28 May 2025
Accepted Manuscript online:
28 May 2025
Article published online:
01 August 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Dobler D, Leitner M, Moor N, Reiser O. Eur J Org Chem 2021; 6180
- 2 McGlacken GP, Fairlamb IJS. Nat Prod Rep 2005; 22: 369
- 3 Praveen C, Ayyanar A, Perumal PT. Bioorg Med Chem Lett 2011; 21: 4170
- 4 Pattenden G, Pegga NA, Kenyon RW. J Chem Soc, Perkin Trans 1991; 1: 2363
- 5 Fedin VV, Obydennov DL, Usachev SA, Sosnovskikh VY. Organ 2023; 4: 539
- 6 Usachev BI. J Fluor Chem 2015; 175: 36
- 7 Vraničar L, Požgan F, Polanc S, Kočevar M. Amino Acids 2003; 24: 273
- 8 Points III GL, Beaudry CM. Org Lett 2021; 23: 6882
- 9 Points III GL, Stout KT, Beaudry CM. Chem – Eur J 2020; 26: 16655
- 10 Giese S, Klimov K, Mikeházi A. et al. Angew Chem Int Ed 2021; 60: 3581
- 11 Kranjc K, Štefane B, Polanc S, Kočevar M. J Org Chem 2004; 69: 3190
- 12 Kranjc K, Kočevar M. Bull Chem Soc Jpn 2001; 2007: 80
- 13 Chu X-P, Zhou Q-F, Zhao S. et al. Chin Chem Lett 2013; 24: 120
- 14 Zhou Q-F, Zhu Y, Tang W-F, Lu T. Synthesis 2010; 2: 211
- 15 Požgan F, Kranjc K, Kepe V, Polanc S, Kočevar M. ARKIVOC 2007; viii: 97
- 16 Tolmachova NA, Dolovanyuk VG, Gerus II. et al. Synthesis 2011; 7: 1149
- 17 Fan W, Ma S. Angew Chem Int Ed 2014; 53: 14542
- 18 Nakahama K, Suzuki M, Ozako M, Mizota I, Shimizu M, Asian J. Org Chem 2018; 7: 910
- 19 Zhu Y, Gong Y. J Org Chem 2015; 80: 490
- 20 Arshada JZ, Hanif M. RSC Med Chem 2022; 13: 1127
- 21 Ahmad T, Rasheed T, Hussain M, Rizwan K. Top Curr Chem 2021; 379: 38
- 22 He M, Fan M, Peng Z, Wang G. Eur J Med Chem 2021; 221: 113546
- 23 Jessen HJ, Gademann K. Nat Prod Rep 2010; 27: 1168
- 24 Sangwan S, Yadav N, Kumar R. et al. Eur J Med Chem 2022; 232: 114199
- 25 Zhang Y, Pike A. Bioorg Med Chem Letters 2021; 38: 127849
- 26 Lin S, Liu C, Zhao X. et al. Front Chem 2022; 10: 869860
- 27 Cilibrizzi A, Abbate V, Chen Y-L, Ma Y, Zhou T, Hider RC. Chem Rev 2018; 118: 7657
- 28 Santos MA, Marques SM, Chaves S. Coord Chem Rev 2012; 256: 240
- 29 Santos MA, Chaves S. Fut Med Chem 2015; 7: 383
- 30 Cusnir R, Imberti C, Hider RC, Blower PJ, Ma MT. Int J Mol Sci 2017; 18: 116
- 31 Jiang X, Zhou T, Bai R, Xie Y. J Med Chem 2020; 63: 14470
- 32 Shalbi F, Ali AR. Eur J Med Chem 2024; 279: 116900
- 33 Singh S, Kumari N, Kanungo BK, Baral M. Sens Diagn 2024; 3: 968
- 34 Ke D, Zhang L, Zhong X, Shao J, Yu Y, Chen W. Org Lett 2022; 24: 1263
- 35 Kožul M, Stiplošek Z, Orhanovič Z, Jakopčić K, Nagl A, Hergold-Brundić A. J Heterocycl Chem 1993; 36: 493
- 36 Jakopčić K, Kojič J, Orhanović Z, Stiplošek Z, Nagl A, Hergold A. J Heterocycl Chem 1992; 29: 107
- 37 Das AJ, Das SK. Eur J Org Chem 2022; e202101034
- 38 Nonn M, Remete AM, Fülöp F, Kiss L. Tetrahedron 2024; 73: 5461
- 39 Mamedova VL, Khikmatova GZ, Korshin DE, Mamedova SV, Gavrilova EL, Mamedov VA. Russ Chem Rev 2022; 91: RCR5049
- 40 Steparuk EV, Meshcheryakova EA, Viktorova VV, Ulitko MV, Obydennov DL, Sosnovskikh VY. J Org Chem 2023; 88: 11590
- 41 Wu W, He S, Zhou X, Lee C-S. Eur J Org Chem 2010; 1124
- 42 Reddy TN, Beatriz A, Rao VJ, de Lima DP. Chem Asian J 2019; 14: 344
- 43 Palacios F, Vicario J, Aparicio D. Eur J Org Chem 2006; 2843
- 44 Murguly E, Norsten TB, Branda N. J Chem Soc, Perkin Trans 2 1999; 2789
- 45 Baranac-Stojanović M, Aleksić J, Stojanović M. Org Biomol Chem 2024; 22: 144
- 46 Obydennov DL, Simbirtseva AE, Piksin SE, Sosnovskikh VY. ACS Omega 2020; 5: 33406
- 47 Viktorova VV, Obydennov DL, Mustafina AF, Ulitko MV, Kornev MY, Sosnovskikh VY. Org Biomol Chem 2025; 23: 2206
- 48 Hoeksema H, Mizsak SA, Baczynskyj L, Pscbigoda LM. J Am Chem Soc 1982; 104: 5173
- 49 Steparuk EV, Obydennov DL, Sosnovskikh VY. Molbank 2023; 2023: M1668
- 50 Kolehmainena E, Borys Osmialowski B. Int Rev Phys Chem 2012; 31: 567
- 51 Sheldrick GM. Acta Crystallogr Sect A: Found Crystallogr 2008; 64: 112
- 52 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H. J Appl Crystallogr 2009; 42: 339