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
Synthesis 2022; 54(07): 1765-1774
DOI: 10.1055/a-1628-5304
DOI: 10.1055/a-1628-5304
paper
Group-Assisted-Purification Chemistry Strategy for the Efficient Assembly of Cyclic Fused Pyridinones
This project was supported by the Zhejiang Provincial Natural Science Foundation of China under Grant No. LD21H300001 to Y. Yu, and Zhejiang University special scientific research fund for COVID-19 prevention and control to W. Chen.
Abstract
A group-assisted-purification (GAP) chemistry strategy-based Ugi four-center three-component reaction (Ugi-4C-3CR) was explored. The reaction proceeded well to deliver the cyclic fused pyridinones selectively. Moreover, the reaction conditions were mild and avoided additional chromatography or recrystallization workup. Also, wide variations in substrates, such as anilines and aliphatic amines as well as amino alcohols and amino acid esters were all tolerated and pyridinones are achieved in good to excellent yields. Importantly, ladder-type cyclic fused pyridinones can be further constructed in excellent yield of 91%.
Key words
group-assisted-purification (GAP) chemistry - cyclic fused pyridinones - gram-scale synthesis - high atom efficiency - good functional group toleranceSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1628-5304.
- Supporting Information
Publication History
Received: 16 July 2021
Accepted after revision: 01 September 2021
Accepted Manuscript online:
01 September 2021
Article published online:
04 November 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Rohde JM, Karavadhi S, Pragani R, Liu L, Fang Y, Zhang W, McIver A, Zheng H, Liu Q, Davis MI, Urban DJ, Lee TD, Cheff DM, Hollingshead M, Henderson MJ, Martinez NJ, Brimacombe KR, Yasgar A, Zhao W, Klumpp-Thomas C, Michael S, Covey J, Moore WJ, Stott GM, Li Z, Simeonov A, Jadhav A, Frye S, Hall MD, Shen M, Wang X, Patnaik S, Boxer MB. J. Med. Chem. 2021; 64: 4913
- 2 Chen W, Yuan X, Li Z, Lu Z, Kong S, Jiang H, Du H, Pan X, Nandi M, Kong X, Brown K, Liu Z, Zhang G, Hider RC, Yu Y. J. Med. Chem. 2020; 63: 4215
- 3 Jiang X, Zhou T, Bai R, Xie Y. J. Med. Chem. 2020; 63: 14470
- 4 Credille CV, Morrison CN, Stokes RW, Dick BL, Feng Y, Sun J, Chen Y, Cohen SM. J. Med. Chem. 2019; 62: 9438
- 5 Cilibrizzi A, Abbate V, Chen YL, Ma Y, Zhou T, Hider RC. Chem. Rev. 2018; 118: 7657
- 6 Abbate V, Reelfs O, Kong X, Pourzand C, Hider RC. Chem. Commun. 2016; 52: 784
- 7 Tanis SP, Strohbach JW, Parker TT, Moon MW, Thaisrivongs S, Perrault WR, Hopkins TA, Knechtel ML, Oien NL, Wieber JL, Stephanski KJ, Wathen MW. Bioorg. Med. Chem. Lett. 2010; 20: 1994
- 8 Ma Y, Luo W, Camplo M, Liu Z, Hider RC. Bioorg. Med. Chem. Lett. 2005; 15: 3450
- 9 Miyagawa M, Akiyama T, Taoda Y, Takaya K, Takahashi-Kageyama C, Tomita K, Yasuo K, Hattori K, Shano S, Yoshida R, Shishido T, Yoshinaga T, Sato A, Kawai M. J. Med. Chem. 2019; 62: 8101
- 10 Kawasuji T, Johns BA, Yoshida H, Weatherhead JG, Akiyama T, Taishi T, Taoda Y, Mikamiyama-Iwata M, Murai H, Kiyama R, Fuji M, Tanimoto N, Yoshinaga T, Seki T, Kobayashi M, Sato A, Garvey EP, Fujiwara T. J. Med. Chem. 2013; 56: 1124
- 11 Wang H, Kowalski MD, Lakdawala AS, Vogt FG, Wu L. Org. Lett. 2015; 17: 564
- 12 Hughes DL. Org. Process. Res. Dev. 2019; 23: 716
- 13 Kawasuji T, Johns BA, Yoshida H, Taishi T, Taoda Y, Murai H, Kiyama R, Fuji M, Yoshinaga T, Seki T, Kobayashi M, Sato A, Fujiwara T. J. Med. Chem. 2012; 55: 8735
- 14 Bacchi A, Carcelli M, Compari C, Fisicaro E, Pala N, Rispoli G, Rogolino D, Sanchez TW, Sechi M, Sinisi V, Neamati N. J. Med. Chem. 2011; 54: 8407
- 15 Heo YA. Drugs 2018; 78: 693
- 16 Noshi T, Kitano M, Taniguchi K, Yamamoto A, Omoto S, Baba K, Hashimoto T, Ishida K, Kushima Y, Hattori K, Kawai M, Yoshida R, Kobayashi M, Yoshinaga T, Sato A, Okamatsu M, Sakoda Y, Kida H, Shishido T, Naito A. Antiviral. Res. 2018; 160: 109
- 17 Asahina Y, Hojo H. J. Org. Chem. 2020; 85: 1458
- 18 Riva R. Science 2018; 361: 1072
- 19 Shaabani S, Dömling A. Angew. Chem. Int. Ed. 2018; 57: 16266
- 20 Abdelraheem EM. M, Khaksar S, Kurpiewska K, Kalinowska-Tluscik J, Shaabani S, Dömling A. J. Org. Chem. 2018; 83: 1441
- 21 Ridder B, Mattes DS, Nesterov-Mueller A, Breitling F, Meier MA. R. Chem. Commun. 2017; 53: 5553
- 22 Chen E, Shao JA, Tang P, Shu K, Chen WT, Yu YP. Green Chem. 2018; 20: 3696
- 23 Kaur P, Wever W, Pindi S, Milles R, Gu P, Shi M, Li GG. Green Chem. 2011; 13: 1288
- 24 Kaur P, Pindi S, Wever W, Rajale T, Li G. J. Org. Chem. 2010; 75: 5144
- 25 Group NA. S, Kouanfack C, Mpoudi-Etame M, Omgba Bassega P, Eymard-Duvernay S, Leroy S, Boyer S, Peeters M, Calmy A, Delaporte E. N. Engl. J. Med. 2019; 381: 816