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CC BY 4.0 · SynOpen 2023; 07(02): 258-266
DOI: 10.1055/a-2091-7934
DOI: 10.1055/a-2091-7934
paper
Temperature-Controlled Diastereoselective Doebner/Ugi Tandem Reaction
The project of National Research Foundation of Ukraine ‘Polypharmacophoric organic compounds based on peptidomimetics and fused benzodiazepines’ (2020.02/0023), and the Royal Society of Chemistry (grant R22-1038807649).
Abstract
Novel peptidomimetics containing a pyrrolone fragment were synthesized by a tandem combination of Doebner and Ugi type multicomponent reactions with controlled diastereoselectivity. This approach represents a convenient synthesis in the temperature range from 25 to 45 °C. In most cases, the new method allowed each diastereomer to be isolated separately.
Keywords
multicomponent reactions - Doebner reaction - Ugi reaction - peptidomimetics - pyrrolones - diastereoselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2091-7934.
- Supporting Information
Publication History
Received: 19 April 2023
Accepted after revision: 10 May 2023
Accepted Manuscript online:
11 May 2023
Article published online:
31 May 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Graebin CS, Ribeiro FV, Rogério KR, Kümmerle AE. Curr. Org. Synth. 2019; 16: 855
- 2 John SE, Gulati S, Shankaraiah N. Org. Chem. Front. 2021; 8: 4237
- 3 Murlykina MV, Morozova AD, Zviagin IM, Sakhno YI, Desenko SM, Chebanov VA. Front. Chem. 2018; 527
- 4 Multicomponent Reactions towards Heterocycles . Van der Eycken E, Sharma UK. Wiley; Weinheim: 2022
- 5 Younus HA, Al-Rashida M, Hameed A, Uroos M, Salar U, Rana S, Khan KM. Expert Opin. Ther. Pat. 2021; 31: 267
- 6 Uchiro H, Shionozaki N, Tanaka R, Kitano H, Iwamura N, Makino K. Tetrahedron Lett. 2013; 54: 506
- 7 Tanaka R, Ohishi K, Takanashi N, Nagano T, Suizu H, Suzuki T, Kobayashi S. Org. Lett. 2012; 14: 4886
- 8 Khalaf AI, Waigh RD, Drummond AJ, Pringle B, McGroarty I, Skellern GG, Suckling CJ. J. Med. Chem. 2004; 47: 2133
- 9 Gein VL, Popov AV, Kolla V, Popova NA, Potemkin KD. Pharm. Chem. J. 1993; 27: 343
- 10 Gein VL, Popov AV, Kolla WE, Popova NA. Pharmazie 1993; 48: 107
- 11 Alizadeh N, Hossein Sayahi M, Iraji A, Yazzaf R, Moazzam A, Mobaraki K, Adib M, Attarroshan M, Larijani B, Rastegar H, Khoshneviszadeh M, Mahdavi M. Bioorg. Chem. 2022; 126: 105876
- 12 Bhajammanavar V, Mallik S, Baidya M. Org. Biomol. Chem. 2019; 17: 1740
- 13 Joksimović N, Petronijević J, Milović E, Janković N, Baskić D, Popović S, Todorović D, Matić S, Vraneš M, Tot A. Med. Chem. 2022; 18: 337
- 14 del Corte X, López-Francés A, Villate-Beitia I, Sainz-Ramos M, Martínez de Marigorta E, Palacios F, Alonso C, de los Santos JM, Pedraz JL, Vicario J. Pharmaceuticals 2022; 15: 511
- 15 Castellano TG, Neo AG, Marcaccini S, Marcos CF. Org. Lett. 2012; 14: 6218
- 16 Nunes PS. G, Vidal HD. A, Corrêa AG. Org. Biomol. Chem. 2020; 18: 7751
- 17 Zhu D, Xia L, Pan L, Li S, Chen R, Mou Y, Chen X. J. Org. Chem. 2012; 77: 1386
- 18 Lambruschini C, Moni L, Banfi L. Eur. J. Org. Chem. 2020; 3766
- 19 Riva R. Science 2018; 361: 1072
- 20 Zhang J, Yu P, Li S.-Y, Sun H, Xiang S.-H, Wang J, Houk KN, Tan B. Science 2018; 361: eaas8707 ; DOI: 10.1126/science.aas8707
- 21 Murlykina MV, Kolomiets OV, Kornet MM, Sakhno YI, Desenko SM, Dyakonenko VV, Shishkina SV, Brazhko OA, Musatov VI, Tsygankov AV, van der Eycken EV, Chebanov VA. Beilstein J. Org. Chem. 2019; 15: 1281
- 22 Sakhno YI, Radchenko OV, Muravyova EA, Sirko SM, Shishkina SV, Musatov VI, Desenko SM, Chebanov VA. Chem. Heterocycl. Compd. 2021; 57: 261
- 23 de Koning CB, van Otterlo WA, Michael JP. Tetrahedron 2003; 59: 8337
- 24 Kessler H. Angew. Chem., Int. Ed. Engl. 1970; 9: 219
- 25 Ōki M. The Chemistry of Rotational Isomers. In Reactivity and Structure Concepts in Organic Chemistry, Vol. 30. Springer; Berlin: 1993
- 26 Akkit JW. NMR and Chemistry: An Introduction to Modern NMR Spectroscopy, Third Edition. Akitt JW. Chapman & Hall; London: 1993
- 27 Shyshkina MO, Sakhno YI, Radchenko OV, Shishkina SV, Desenko SM, Chebanov VA. Acta Crystallogr., Sect. E: Crystallogr. Commun. 2021; 77: 1208
- 28 Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008; 64: 112