A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination–Cyclization Approach

Henry P. Caldora; Sebastian Govaerts; Shashikant U. Dighe; Oliver J. Turner; Daniele Leonori

doi:10.1055/a-1538-8429

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(22): 4272-4278
DOI: 10.1055/a-1538-8429

special topic

Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

A de novo Synthesis of Oxindoles from Cyclohexanone-Derived γ-Keto-Ester Acceptors Using a Desaturative Amination–Cyclization Approach

Henry P. Caldora‡

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

,

Sebastian Govaerts‡

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

,

Shashikant U. Dighe

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

,

Oliver J. Turner

^bOncology R&D, Research & Early Development, AstraZeneca, Darwin building, 310, Cambridge Science Park, Milton Road, Cambridge CB4 0WG, UK

,

Daniele Leonori ∗

^aDepartment of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Dedicated to Prof Sarah Reisman in recognition on her award of the inaugural Margaret Faul Women in Chemistry Award.

Abstract

Here we report a desaturative approach for oxindole synthesis. This method uses simple ethyl 2-(2-oxocyclohexyl)acetates and primary amine building blocks as coupling partners. A dual photoredox–cobalt manifold is used to generate a secondary aniline that, upon heating, cyclizes with the pendent ester functionality. The process operates under mild conditions and was applied to the modification of several amino acids, the blockbuster drug mexiletine, as well as the formation of dihydroquinolinones.

Key words

photoredox - cobalt catalysis - dehydrogenative amination - late-stage modification - amino acids - oxindole

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References

1a Pennington LD, Moustakas DT. J. Med. Chem. 2017; 60: 3552
1b Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
1c Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
1d Lamberth C. Pest Manage. Sci. 2013; 69: 1106

2a Marti C, Carreira EM. Eur. J. Org. Chem. 2003; 2003: 2209
2b Leoni A, Locatelli A, Morigi R, Rambaldi M. Expert Opin. Ther. Pat. 2016; 26: 149

3a Durbin MJ, Willis MC. Org. Lett. 2008; 10: 1413
3b Jensen T, Madsen R. J. Org. Chem. 2009; 74: 3990
3c Chen W.-T, Wei W.-T. Asian J. Org. Chem. 2018; 7: 1429
3d Reddy CR, Jithender E, Krishna G, Reddy GV, Jagadeesh B. Org. Biomol. Chem. 2011; 9: 3940

4a Singh R, Nagesh K, Yugandhar D, Prasanthi AV. G. Org. Lett. 2018; 20: 4848
4b Marchese AD, Larin EM, Mirabi B, Lautens M. Acc. Chem. Res. 2020; 53: 1605

5a Hennessy EJ, Buchwald SL. J. Am. Chem. Soc. 2003; 125: 12084
5b Li Y, Wang K, Ping Y, Wang Y, Kong W. Org. Lett. 2018; 20: 921
5c Liu C, Liu D, Zhang W, Zhou L, Lei A. Org. Lett. 2013; 15: 6166
5d Yamamoto K, Qureshi Z, Tsoung J, Pisella G, Lautens M. Org. Lett. 2016; 18: 4954

6a Wu Z.-J, Xu H.-C. Angew. Chem. Int. Ed. 2017; 56: 4734
6b Ju X, Liang Y, Jia P, Li W, Yu W. Org. Biomol. Chem. 2012; 10: 498
6c Wei W.-T, Zhou M.-B, Fan J.-H, Liu W, Song R.-J, Liu Y, Hu M, Xie P, Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 3638
6d Meng Y, Guo L.-N, Wang H, Duan X.-H. Chem. Commun. 2013; 49: 7540
6e Wang J.-Y, Zhang X, Bao Y, Xu Y.-M, Cheng X.-F, Wang X.-S. Org. Biomol. Chem. 2014; 12: 5582

7 Nykaza TV, Li G, Yang J, Luzung MR, Radosevich AT. Angew. Chem. Int. Ed. 2020; 59: 4505

8a Shelar SV, Argade NP. Org. Biomol. Chem. 2019; 17: 6671
8b Lv J, Zhang-Negrerie D, Deng J, Du Y, Zhao K. J. Org. Chem. 2014; 79: 1111
8c Jiang X, Zheng C, Lei L, Lin K, Yu C. Eur. J. Org. Chem. 2018; 2018: 1437
8d Hartmann M, Streb C. J. Porous Mater. 2006; 13: 347
8e van Deurzen MP. J, van Rantwijk F, Sheldon RA. J. Mol. Catal. B: Enzym. 1996; 2: 33
8f Takeuchi Y, Tarui T, Shibata N. Org. Lett. 2000; 2: 639
8g Jiang X, Yang J, Zhang F, Yu P, Yi P, Sun Y, Wang Y. Org. Lett. 2016; 18: 3154

9 Dighe SU, Juliá F, Luridiana A, Douglas JJ, Leonori D. Nature 2020; 584: 75

10a Koizumi Y, Jin X, Yatabe T, Miyazaki R, Hasegawa J.-Y, Nozaki K, Mizuno N, Yamaguchi K. Angew. Chem. Int. Ed. 2019; 58: 10893
10b Shimomoto Y, Matsubara R, Hayashi M. Adv. Synth. Catal. 2018; 360: 3297
10c Girard SA, Hu X, Knauber T, Zhou F, Simon M.-O, Deng G.-J, Li C.-J. Org. Lett. 2012; 14: 5606
10d Hajra A, Wei Y, Yoshikai N. Org. Lett. 2012; 14: 5488
10e Ichitsuka T, Komatsuzaki S, Masuda K, Koumura N, Sato K, Kobayashi S. Chem. Eur. J. 2021; in press; DOI:
10f Girard SA, Huang H, Zhou F, Deng G.-J, Li C.-J. Org. Chem. Front. 2015; 2: 279

11 Maeda K, Matsubara R, Hayashi M. Org. Lett. 2021; 23: 1530
12 Nicholas AM. d. P, Arnold DR. Can. J. Chem. 1982; 60: 2165
13 Pirnot MT, Rankic DA, Martin DB. C, MacMillan DW. C. Science 2013; 339: 1593

14a Gridnev AA, Ittel SD. Chem. Rev. 2001; 101: 3611
14b Dempsey JL, Brunschwig BS, Winkler JR, Gray HB. Acc. Chem. Res. 2009; 42: 1995

15 Manolis AS, Deering TF, Cameron J, Markestes NA. III. Clin. Cardiol. 1990; 13: 349

16a Yang BH, Buchwald SL. Org. Lett. 1999; 1: 35
16b Tian X, Li X, Duan S, Du Y, Liu T, Fang Y, Chen W, Zhang H, Li M, Yang X. Adv. Synth. Catal. 2021; 363: 1050
16c Kuang Z, Li B, Song Q. Chem. Commun. 2018; 54: 34
16d Zhang L, Qureshi Z, Sonaglia L, Lautens M. Angew. Chem. Int. Ed. 2014; 53: 13850

17 See SI for more information.
18 Liu L, Song L, Guo Y, Min D, Shi T, Zhang W. Tetrahedron 2018; 74: 354
19 Poondra RR, Turner NJ. Org. Lett. 2005; 7: 863
20 Sumiyoshi T, Enomoto T, Takai K, Takahashi Y, Konishi Y, Uruno Y, Tojo K, Suwa A, Matsuda H, Nakako T, Sakai M, Kitamura A, Uematsu Y, Kiyoshi A. ACS Med. Chem. Lett. 2013; 4: 244

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