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Synthesis 2022; 54(03): 658-666
DOI: 10.1055/a-1649-5317
DOI: 10.1055/a-1649-5317
paper
An Attempt to Achieve Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1,4]Diazepinones Delivers Selective Dopamine D2 Receptor Ligands
This research was supported by the Russian Science Foundation (grant no. 19-75-30008).
Abstract
Attempts to extend the hydrated imidazoline ring expansion (HIRE) strategy to a series of diarene-fused [1,4]diazepinones (earlier applied successfully to bis-pyrido substrate nevirapine) did not result in ring expansion but, rather, led to 2-aminoethyl side chain expulsion. This seeming setback (setting the limitations to the HIRE methodology substrate scope) led to the discovery of selective dopamine D2 ligands with elements of structure–activity relationships.
Key words
[1,4]diazepinones - fused imidazolinium moiety - hydrated imidazoline ring expansion - 2-aminoethyl side chain expulsion - selective dopamine D2 ligandsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1649-5317.
- Supporting Information
Publication History
Received: 04 August 2021
Accepted after revision: 20 September 2021
Accepted Manuscript online:
20 September 2021
Article published online:
27 October 2021
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References
- 1 Zhao C, Ye Z, Ma Z.-x, Wildmaan SA, Blaszczyk SA, Hu L, Guizei IA, Tang W. Nat. Commun. 2019; 10: 4015
- 2a Yet L. Chem. Rev. 2000; 100: 2963
- 2b Molander GA. Acc. Chem. Res. 1998; 31: 603
- 2c Illuminati G, Mandolini L. Acc. Chem. Res. 1981; 14: 95
- 2d Galli C, Mandolini L. Eur. J. Org. Chem. 2000; 3117
- 2e Sharma A, Appukkuttan P, Van der Eycken E. Chem. Commun. 2012; 48: 1623
- 3a Reutskaya E, Sapegin A, Peintner S, Erdélyi M, Krasavin M. J. Org. Chem. 2021; 86: 5778
- 3b Grintsevich S, Sapegin A, Reutskaya E, Peintner S, Erdélyi M, Krasavin M. Eur. J. Org. Chem. 2020; 5664
- 3c Sapegin A, Osipyan A, Krasavin M. Org. Biomol. Chem. 2017; 15: 2906
- 3d Osipyan A, Sapegin A, Novikov A, Krasavin M. J. Org. Chem. 2018; 83: 9707
- 3e Grintsevich S, Sapegin A, Reutskaya E, Krasavin M. Tetrahedron Lett. 2019; 60: 20
- 4 Lavit K, Reutskaya E, Grintsevich S, Sapegin A, Krasavin M. Tetrahedron Lett. 2020; 61: 152423
- 5 Slifirski G, Krol M, Kleps J, Ulenberg S, Belka M, Baczek T, Siwek A, Stachowicz K, Szewczyk B, Nowak G, Bojarski A, Kozioł AE, Turło J, Herrold F. Eur. J. Med. Chem. 2019; 166: 144
- 6 Beaulieu JM, Gainetdinov RR. Pharmacol. Rev. 2011; 63: 182