RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis
DOI: 10.1055/a-2705-5658
DOI: 10.1055/a-2705-5658
Feature
Published as part of the Special Topic Dedicated to Prof. H. Ila
Acid-Catalyzed Regioselective 1,6-Conjugate Addition of Mercaptopyridine/Hydroxypyridine to Para-Quinone Methides
Autoren
Gefördert durch: UGC New Delhi JUNE-18-144311,SUR/2022/000608
Gefördert durch: ATS
Funding Information UGC New Delhi for research fellowships (JUNE-18-144311). SBW thanks the SERB-SURE project SUR/2022/000608 for financial support.
Abstract
This protocol describes a trifluoroacetic acid-catalyzed regioselective 1,6-conjugate addition of mercaptopyridine and hydroxypyridine to para-quinone methides. The present reactions exhibit superior results in terms of regioselectivity, mild reaction conditions, straightforward workup (no column chromatography purification), and broad substrate scope with good functional-group compatibility. This efficient method enables the synthesis of trisubstituted methanes with pyridone and sulfide core structures.
Publikationsverlauf
Eingereicht: 23. Juni 2025
Angenommen nach Revision: 29. August 2025
Accepted Manuscript online:
19. September 2025
Artikel online veröffentlicht:
10. November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Jacob C. Nat Prod Rep 2006; 23: 851
- 1b Jiang CS, Müller WEG, Schröder HC, Guo Y-W. Chem Rev 2012; 112: 2179
- 1c Ilardi EA, Vitaku E, Njardarson JT. J Med Chem 2014; 57: 2832
- 1d Fontecave M, Ollagnier-de-Choudens S, Mulliez E. Chem Rev 2003; 103: 2149
- 1e Xie J, Liao B, Tang R-Y. J Agric Food Chem 2020; 68: 12505
- 2a Du L, Robles AJ, King JB. et al. Angew Chem Int Ed 2014; 53: 804
- 2b Forrestall KL, Burley DE, Cash MK, Pottie IR, Darvesh S. Chem-Biol Interact 2021; 335: 109348
- 2c Jessen HJ, Gademann K. Nat Prod Rep 2010; 27: 1168
- 3a Lin S, Liu C, Zhao X. et al. Front Chem. 2022
- 3b Sangwan S, Yadav N, Kumar R. et al. Eur J Med Chem 2022; 232: 114199
- 3c Zhang Y, Pike A. Bioorg Med Chem Lett 2021; 38: 127849
- 3d Hirano K, Miura M. Chem Sci 2018; 9: 22
- 3e Hurtado-Rodríguez D, Salinas-Torres A, Rojas H, Becerra D, Castillo JC. RSC Adv 2022; 12: 35158
- 3f Kung PP, Fan C, Gukasyan HJ. et al. J Med Chem 2021; 64: 1725
- 3g Sarkar S, Bridwell AEM, Good JAD. et al. J Med Chem 2023; 66: 11056
- 3h Yadav N, Sangwan S, Kumar R. et al. ChemistrySelect 2021; 6: 11792
- 4a Wang J-Y, Hao W-J, Tu SJ, Jiang B. Org Chem Front 2020; 7: 1743
- 4b Yang M, Han H, Jiang H, Ye S, Fan X, Wu J. Chin Chem Lett 2021; 32: 3535
- 4c Wang J, Zhao L, Zhu C. et al. Chin Chem Lett 2022; 33: 4549
- 4d Xu S, Xie J, Liu Y. et al. J Org Chem 2021; 86: 14983
- 4e Vaishanv NK, Gupta AK, Kant R, Mohanan K. J Org Chem 2018; 83: 8759
- 5a Venkatesh R, Shankar G, Narayanan AC, Modi G, Sabiah S, Kandasamy J. J Org Chem 2022; 87: 6730
- 5b Kotha S, Gupta NK, Solanke BU. ChemistrySelect 2023; 8: e202302672
- 5c Shuai M-S, Guan X, Fei X-H. et al. RSC Adv 2023; 13: 12982
- 5d Azeem Z. Mandal J Org Chem 2023; 88: 1695
- 5e Zhong Y, Li G, Zhang D. et al. Eur J Org Chem 2024; 27: e202400130
- 5f Mei Y-T, Zhang H, Jiang Y. et al. Chem Commun 2024; 60: 8589
- 6 Roy D, Panda G. Synthesis 2019; 51: 4434
- 7 Ren H-X, Zhang Y, Wang H-L. J Heterocycl Chem 2020; 57: 4322
- 8 Xiu H, Li T, Song C, Ma Y. Eur J Org Chem 2020; 6068-6072
- 9 Akyildiz V, Saracoglu N, Asian J. Org Chem 2023; 12: e202300121
- 10 Kaur N, Singh P, Banerjee P. Adv Synth Catal 2021; 363: 2813
- 11 Dash R, Hota SK, Murarka S. Synthesis 2024; 56: 677-685
- 12 Ma S, Chen M, Yang Z, Liu X, Cao H. Adv Synth Catal 2003; 2024: 366
- 13 Rai V, Kavyashree P, Harmalkar SS, Dhuric SN, Maddani RM. Org Biomol Chem 2022; 20: 345
- 14 Guin S, Saha HK, Patel AK, Gudimella SK, Biswas S, Samanta S. Tetrahedron 2020; 76: 131338
- 15 More SG, Rupanawar BD, Suryavanshi G. J Org Chem 2021; 86: 10129
- 16 Song R, Zhuo C, Si W. et al. Adv Synth Catal 2022; 364: 4069
- 17 Sharma RS, Singh G, Anand RV. ACS Org Inorg Au 2022; 2: 186
- 18 Turbedaroglu O, Lafzi F, Kilic H. Chem Commun 2022; 58: 4893
- 19 Qi S-S, Luo X, Sun X-P. et al. Chem Commun 2023; 59: 8822
- 20a Gaikwad RA, Kamble SB, Waghmode SB. Chem-Asian J 2022; 17: e202200931
- 20b Gaikwad RA, Savekar AT, Waghmode SB. J Org Chem 2023; 88: 9987
- 20c Savekar AT, Gaikwad RA, Waghmode SB. J Org Chem 2024; 89: 9389
- 20d Savekar AT, Karande VB, Hingane DG, Waghmode SB. Org Biomol Chem 2024; 22: 8945
- 20e Mane BB, Savekar AT, Waghmode SB. Org Lett 2025; 27: 2554-2558
- 21 Venkatesh R, Gurukkalot K, Rajendran V, Kandasamy J. Org Biomol Chem 2025; 23: 383
- 22 Breugst M, Mayr H. J Am Chem Soc 2010; 132: 15380-15389