A Journey in the Catalytic Synthesis of 3-Substituted 3-Amino­oxindoles

Jin-Sheng Yu; Feng Zhou; Yun-Lin Liu; Jian Zhou

doi:10.1055/s-0034-1378873

Synlett, Table of Contents

Synlett 2015; 26(18): 2491-2504
DOI: 10.1055/s-0034-1378873

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A Journey in the Catalytic Synthesis of 3-Substituted 3-Aminooxindoles

Authors

Jin-Sheng Yu

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. of China Email: jzhou@chem.ecnu.edu.cn
Feng Zhou

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. of China Email: jzhou@chem.ecnu.edu.cn
Yun-Lin Liu

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. of China Email: jzhou@chem.ecnu.edu.cn
Jian Zhou*

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, P. R. of China Email: jzhou@chem.ecnu.edu.cn

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

Abstract

All articles of this category

Abstract

3-Substituted 3-aminooxindoles represent a type of privileged scaffold widely present in natural products and pharmaceutically active compounds. Thus, their efficient construction is of current interest. This account describes our efforts in the development of new strategies and reactions for facile access to this prominent framework.

1 Introduction

2 Nucleophilic Addition to Isatin Ketimines

3 Direct Amination of 3-Substituted Oxindoles

4 Substitution Reactions of 3-Hydroxyoxindoles

5 Conclusion and Outlook

Key words

3-substituted 3-aminooxindoles - isatin ketimines - aminations - substitution reactions - nucleophilic additions

Full Text

References

References

For reviews, see:

1a Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
1b Shen K, Liu X, Lin L, Feng X. Chem. Sci. 2012; 3: 327
1c Dalpozzo R, Bartoli G, Bencivenni G. Chem. Soc. Rev. 2012; 41: 7247
1d Chauhan P, Chimni SS. Tetrahedron: Asymmetry 2013; 24: 343
1e Cao Z.-Y, Wang Y.-H, Zeng X.-P, Zhou J. Tetrahedron Lett. 2014; 55: 2571
1f Cao Z.-Y, Zhou J. Org. Chem. Front. 2015; 2: 849

2a Anthoni U, Chevolot L, Larsen C, Nielsen PH, Christophersen C. J. Org. Chem. 1987; 52: 4709
2b Chevolot L, Chevolot A.-M, Gajhede M, Larsen C, Anthoni U, Christophersen C. J. Am. Chem. Soc. 1985; 107: 4542
2c Takayama H, Mori I, Kitajima M, Aimi N, Lajis NH. Org. Lett. 2004; 6: 2945
2d Ochi M, Kawasaki K, Kataoka H, Uchio Y, Nishi H. Biochem. Biophys. Res. Commun. 2001; 283: 1118
2e Kitamura H, Kato A, Esaki T. Eur. J. Pharmacol. 2001; 418: 225
2f Bernard K, Bogliolo S, Ehrenfeld J. Br. J. Pharmacol. 2005; 144: 1037
2g Serradeil-Le Gal C, Sylvain D, Brossard G, Manning M, Simiand J, Gaillard R, Griebel G, Guillon G. Stress 2003; 6: 199
2h Chatterjee AK, Yeung BK. S. Curr. Top. Med. Chem. 2012; 12: 473
2i Rottmann M, McNamara C, Yeung BK. S, Lee MC. S, Zou B, Russell B, Seitz P, Plouffe DM, Dharia NV, Tan J, Cohen SB, Spencer KR, González-Páez GE, Lakshminarayana SB, Goh A, Suwanarusk R, Jegla T, Schmitt EK, Beck H.-P, Brun R, Nosten F, Renia L, Dartois V, Keller TH, Fidock DA, Winzeler EA, Diagana TT. Science 2010; 329: 1175
2j Horoszok L, Leung C, Tomaszewski M, Walpole C. WO2007091946, 2007
2k Crosignani S, Jorand-Lebrun C, Page P, Campbell G, Colovray V, Missotten M, Humbert Y, Cleva C, Arrighi J.-F, Gaudet M, Johnson Z, Ferro P, Chollet A. ACS Med. Chem. Lett. 2011; 2: 644
2l Ali MA, Ismail R, Choon TS, Yoon YK, Wei AC, Pandian S, Kumar RS, Osman H, Manogaran E. Bioorg. Med. Chem. Lett. 2010; 20: 7064
2m Girgis AS. Eur. J. Med. Chem. 2009; 44: 91
2n Periyasami G, Raghunathan R, Surendiran G, Mathivanan N. Bioorg. Med. Chem. Lett. 2008; 18: 2342
2o Bertamino A, Soprano M, Musella S, Rusciano MR, Sala M, Vernieri E, Sarno VD, Limatola A, Carotenuto A, Cosconati S, Grieco P, Novellino E, Illario M, Campiglia P, Gomez-Monterrey I. J. Med. Chem. 2013; 56: 5407
2p Vintonyak VV, Warburg K, Kruse H, Grimme S, Hübel K, Rauh D, Waldmann H. Angew. Chem. Int. Ed. 2010; 49: 5902

3a Otomasu H, Natori K, Takahashi H. Chem. Pharm. Bull. 1975; 23: 1431
3b Nishikawa T, Kajii S, Isobe M. Chem. Lett. 2004; 33: 440
3c Miyabe H, Yamaoka Y, Takemoto Y. J. Org. Chem. 2005; 70: 3324
3d Lesma G, Landoni N, Pilati T, Sacchetti A, Silvani A. J. Org. Chem. 2009; 74: 4537
3e Sacchetti A, Silvani A, Gatti FG, Lesma G, Pilati T, Trucchi B. Org. Biomol. Chem. 2011; 9: 5515
3f Lesma G, Meneghetti F, Sacchetti A, Stucchi M, Silvani A. Beilstein J. Org. Chem. 2014; 10: 1383

4a Zhao H, Thurkauf A, Braun J, Brodbeck R, Kieltyka A. Bioorg. Med. Chem. Lett. 2000; 10: 2119
4b Emura T, Esaki T, Tachibana K, Shimizu M. J. Org. Chem. 2006; 71: 8559
4c Ren L, Lian X.-L, Gong L.-Z. Chem. Eur. J. 2013; 19: 3315
4d Cui B.-D, Han W.-Y, Wu Z.-J, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2013; 78: 8833
4e Cui B.-D, You Y, Zhao J.-Q, Zuo J, Wu Z.-J, Xu X.-Y, Zhang X.-M, Yuan W.-C. Chem. Commun. 2015; 51: 757
4f You Y, Cui B.-D, Zhou M.-Q, Zuo J, Zhao J.-Q, Xu X.-Y, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2015; 80: 5951
4g Wang L, Yang D, Li D, Wang R. Org. Lett. 2015; 17: 3004

5a Jia Y.-X, Hillgren JM, Watson EL, Marsden SP, Kündig EP. Chem. Commun. (Cambridge) 2008; 4040
5b Marsden SP, Watson EL, Raw SA. Org. Lett. 2008; 10: 2905
5c Watson EL, Marsden SP, Raw SA. Tetrahedron Lett. 2009; 50: 3318

6a Magnus P, Turnbull R. Org. Lett. 2006; 8: 3497
6b Zhang H, Zhang S.-J, Zhou Q.-Q, Dong L, Chen Y.-C. Beilstein J. Org. Chem. 2012; 8: 1241
6c Sun X.-H, Peng J, Zhang S.-Y, Zhou Q.-Q, Dong L, Chen Y.-C. Acta Chim. Sinica 2012; 70: 1682

For catalytic asymmetric reactions based on N-aryl-substituted isatin ketimines, see:

7a Guo Q.-X, Liu Y.-W, Li X.-C, Zhong L.-Z, Peng Y.-G. J. Org. Chem. 2012; 77: 3589
7b Liu Z, Feng X, Du H. Org. Lett. 2012; 14: 3154
7c Zhang B, Feng P, Sun L.-H, Cui Y, Ye S, Jiao N. Chem. Eur. J. 2012; 18: 9198

For reactions based on N-Boc-substituted isatin ketimines, see:

7d Yan W, Wang D, Feng J, Li P, Zhao D, Wang R. Org. Lett. 2012; 14: 2512
7e Feng J, Yan W, Wang D, Li P, Sun Q, Wang R. Chem. Commun. 2012; 48: 8003
7f Hara N, Nakamura S, Sano M, Tamura R, Funahashi Y, Shibata N. Chem. Eur. J. 2012; 18: 9276
7g Wang D, Liang J, Feng J, Wang K, Sun Q, Zhao L, Li D, Yan W, Wang R. Adv. Synth. Catal. 2013; 355: 548
7h Hu F.-L, Wei Y, Shi M, Pindi S, Li G. Org. Biomol. Chem. 2013; 11: 1921
7i Nakamura S, Hyodo K, Nakamura M, Nakane D, Masuda H. Chem. Eur. J. 2013; 19: 7304
7j Chen X, Chen H, Ji X, Jiang H, Yao Z.-J, Liu H. Org. Lett. 2013; 15: 1846
7k Takizawa S, Rémond E, Arteaga FA, Yoshida Y, Sridharan V, Bayardon J, Jugé S, Sasai H. Chem. Commun. 2013; 49: 8392
7l Wang X.-B, Li T.-Z, Sha F, Wu X.-Y. Eur. J. Org. Chem. 2014; 2014: 739
7m Rajasekaran T, Karthik G, Sridhar B, Kumar SK, Reddy BV. S. Eur. J. Org. Chem. 2014; 2014: 2221
7n Mei L.-Y, Tang X.-Y, Shi M. Org. Biomol. Chem. 2014; 12: 1149
7o George J, Sridhar B, Reddy BV. S. Org. Biomol. Chem. 2014; 12: 1595
7p Holmquist M, Blay G, Pedro JR. Chem. Commun. 2014; 50: 9309
7q Kumar A, Kaur J, Chimni SS, Jassa AK. RSC Adv. 2014; 4: 24816
7r Arai T, Matsumura E, Masu H. Org. Lett. 2014; 16: 2768
7s Fang B, Liu X, Zhao J, Tang Y, Lin L, Feng X. J. Org. Chem. 2015; 80: 3332
7t Montesinos-Magraner M, Vila C, Cantón R, Blay G, Fernández I, Muñoz MC, Pedro JR. Angew. Chem. Int. Ed. 2015; 54: 6320
7u Arai T, Tsuchiya K, Matsumura E. Org. Lett. 2015; 17: 2416
7v Li T.-Z, Wang X.-B, Sha F, Wu X.-Y. Tetrahedron 2013; 69: 7314
7w Nakamura S, Takahashi S, Nakane D, Masuda H. Org. Lett. 2015; 17: 106
7x Beceño C, Chauhan P, Rembiak A, Wang A, Enders D. Adv. Synth. Catal. 2015; 357: 672

For selected examples, see:

8a Cheng L, Liu L, Wang D, Chen Y.-J. Org. Lett. 2009; 11: 3874
8b Bui T, Borregan M, Barbas CF. III. J. Org. Chem. 2009; 74: 8935
8c Yang Z, Wang Z, Bai S, Shen K, Chen D, Liu X, Lin L, Feng X. Chem. Eur. J. 2010; 16: 6632
8d Mouri S, Chen Z, Mitsunuma H, Furutachi M, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 1255
8e Bui T, Hernández-Torres G, Milite C, Barbas CF. III. Org. Lett. 2010; 12: 5696
8f Shen K, Liu X, Wang G, Lin L, Feng X. Angew. Chem. Int. Ed. 2011; 50: 4684
8g Zhang T, Cheng L, Liu L, Wang D, Chen Y.-J. Tetrahedron: Asymmetry 2010; 21: 2800
8h Jia L.-N, Huang J, Peng L, Wang L.-L, Bai J.-F, Tian F, He G.-Y, Xu X.-Y, Wang L.-X. Org. Biomol. Chem. 2012; 10: 236
8i Companyó X, Valero G, Pineda O, Calvet T, Font-Bardía M, Moyano A, Rios R. Org. Biomol. Chem. 2012; 10: 431

9a Yu J.-S, Liu Y.-L, Tang J, Wang X, Zhou J. Angew. Chem. Int. Ed. 2014; 53: 9512
9b Liu Y.-L, Liao F.-M, Niu Y.-F, Zhao X.-L, Zhou J. Org. Chem. Front. 2014; 1: 742
9c Cao Z.-Y, Wang X, Tan C, Zhao X.-L, Zhou J, Ding K. J. Am. Chem. Soc. 2013; 135: 8197
9d Liu Y.-L, Wang X, Zhao Y.-L, Zhu F, Zeng X.-P, Chen L, Wang C.-H, Zhao X.-L, Zhou J. Angew. Chem. Int. Ed. 2013; 52: 13735
9e Zhou F, Tan C, Tang J, Zhang Y.-Y, Gao W.-M, Wu H.-H, Yu Y.-H, Zhou J. J. Am. Chem. Soc. 2013; 135: 10994
9f Cao Z.-Y, Zhou F, Yu Y.-H, Zhou J. Org. Lett. 2013; 15: 42
9g Liu Y.-L, Zhu F, Wang C.-H, Zhou J. Chin. J. Org. Chem. 2013; 33: 1595
9h Liu Y.-L, Zhou J. Chem. Commun. 2012; 48: 1919
9i Zhu F, Zhou F, Cao Z.-Y, Wang C, Zhang Y.-X, Wang C.-H, Zhou J. Synthesis 2012; 44: 3129
9j Yu J.-S, Zhou F, Liu Y.-L, Zhou J. Beilstein J. Org. Chem. 2012; 8: 1360
9k Cao Z.-Y, Zhang Y, Ji C.-B, Zhou J. Org. Lett. 2011; 13: 6398
9l Zhou F, Cao Z.-Y, Zhang J, Yang H.-B, Zhou J. Chem. Asian J. 2012; 7: 233
9m Liu Y.-L, Zhou F, Cao J.-J, Ji C.-B, Ding M, Zhou J. Org. Biomol. Chem. 2010; 8: 3847
9n Ding M, Zhou F, Qian Z.-Q, Zhou J. Org. Biomol. Chem. 2010; 8: 2912
9o Liu Y.-L, Wang B.-L, Cao J.-J, Chen L, Zhang Y.-X, Wang C, Zhou J. J. Am. Chem. Soc. 2010; 132: 15176

For reviews, see:

10a Noble A, Anderson JC. Chem. Rev. 2013; 113: 2887
10b Kobayashi S, Mori Y, Fossey JS, Salter MM. Chem. Rev. 2011; 111: 2626
10c Marqués-López E, Merino P, Tejero T, Herrera RP. Eur. J. Org. Chem. 2009; 15: 2401

11a See also ref. 9m.
11b Liu Y.-L, Zhou J. Chem. Commun. 2013; 49: 4421

12a Liu Y.-L, Zeng X.-P, Zhou J. Chem. Asian J. 2012; 7: 1759
12b Ji C.-B, Cao Z.-Y, Wang X, Wu D.-Y, Zhou J. Chem. Asian J. 2013; 8: 877

13a Ding M, Zhou F, Liu Y.-L, Wang C.-H, Zhao X.-L, Zhou J. Chem. Sci. 2011; 2: 2035
13b Gao W.-M, Yu J.-S, Zhao Y.-L, Liu Y.-L, Zhou F, Wu H.-H, Zhou J. Chem. Commun. 2014; 50: 15179
13c Yu J.-S, Liao F.-M, Gao W.-M, Liao K, Zuo R.-L, Zhou J. Angew. Chem. Int. Ed. 2015; 54: 7381

14 Liu Y.-L. Ph.D. dissertation, Construction of fully substituted carbon stereocenters mediated by asymmetric nucleophilic tertiary amine catalysis. East China Normal University; Shanghai, P. R. of China: 2015

15a Cao J.-J, Zhou F, Zhou J. Angew. Chem. Int. Ed. 2010; 49: 4976
15b Chen L, Shi T.-D, Zhou J. Chem. Asian J. 2013; 8: 556
15c Chen L, Du Y, Zeng X.-P, Shi T.-D, Zhou F, Zhou J. Org. Lett. 2015; 17: 1557
15d Zhu F, Xu P.-W, Zhou F, Wang C.-H, Zhou J. Org. Lett. 2015; 17: 972

For a recent review, see:

15e Zhou J. Multicatalyst System in Asymmetric Catalysis. John Wiley & Sons; New York: 2014. Chapter 9

For reviews of Strecker reactions, see:

16a Liu Y.-L, Zhou J. Synthesis 2015; 47: 1210
16b Wang J, Liu X, Feng X. Chem. Rev. 2011; 111: 6947
16c Merino P, Marqués-López E, Tejero T, Herrera RP. Tetrahedron 2009; 65: 1219

17a Wang Y.-H, Liu Y.-L, Cao Z.-Y, Zhou J. Asian J. Org. Chem. 2014; 3: 429
17b Wang Y.-H, Cao Z.-Y, Niu Y.-F, Zhao X.-L, Zhou J. Acta Chim. Sinica 2014; 72: 867

For reviews, see:

18a Arrayás RG, Carretero JC. Chem. Soc. Rev. 2009; 38: 1940
18b Viso A, Fernández de la Pradilla R, García A, Flores A. Chem. Rev. 2005; 105: 3167

For reviews, see:

19a Ball-Jones NR, Badillo JJ, Franz AK. Org. Biomol. Chem. 2012; 10: 5165
19b Hong L, Wang R. Adv. Synth. Catal. 2013; 355: 1023
19c Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540
19d Cheng D, Ishihara Y, Tan B, Barbas CF. III. ACS Catal. 2014; 4: 743
19e See also ref. 1c.

20 Shi F, Tao Z.-L, Luo S.-W, Tu S.-J, Gong L.-Z. Chem. Eur. J. 2012; 18: 6885

21a Duce S, Pesciaioli F, Gramigna L, Bernardi L, Mazzanti A, Ricci A, Bartoli G, Bencivenni G. Adv. Synth. Catal. 2011; 353: 860
21b Badillo JJ, Silva-Garcia A, Shupe BH, Fettinger JC, Franz AK. Tetrahedron Lett. 2011; 52: 5550
21c Zhang B, Feng P, Sun L.-H, Cui Y, Ye S, Jiao N. Chem. Eur. J. 2012; 18: 9198
21d Shi F, Xing G.-J, Zhu R.-Y, Tan W, Tu S. Org. Lett. 2013; 15: 128

22 Yin X.-P, Zeng X.-P, Liu Y.-L, Liao F.-M, Yu J.-S, Zhou F, Zhou J. Angew. Chem. Int. Ed. 2014; 53: 13740

For a review, see:

23a Thompson S, Coyne AG, Knipe PC, Smith MD. Chem. Soc. Rev. 2011; 40: 4217

For examples, see:

23b Müller S, List B. Angew. Chem. Int. Ed. 2009; 48: 9975
23c Maciver EE, Thompson S, Smith MD. Angew. Chem. Int. Ed. 2009; 48: 9979
23d Maciver EE, Knipe PC, Cridland AP, Thompson AL, Smith MD. Chem. Sci. 2012; 3: 537

24 Zhou J. Multicatalyst System in Asymmetric Catalysis. John Wiley & Sons; New York: 2014
25 Yamasaki S, Fujii K, Wada R, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2002; 124: 6536

For reviews, see:

26a Hosomi A. Acc. Chem. Res. 1988; 21: 200
26b Denmark SE, Fu J. Chem. Rev. 2003; 103: 2763
26c Shibasaki M, Kanai M. Chem. Rev. 2008; 108: 2853

For reviews, see:

27a Zhou F, Liao F.-M, Yu J.-S, Zhou J. Synthesis 2014; 46: 2983
27b Russo A, Fusco CD, Lattanzi A. RSC Adv. 2012; 2: 385
27c Xu X, Cheng G, Li X. Chin. J. Org. Chem. 2012; 32: 1024
27d Smith AM. R, Hii KK. Chem. Rev. 2011; 111: 1637
27e Vallribera A, Maria SR, Shafir A. Curr. Org. Chem. 2011; 15: 1539
27f Kanzian T, Mayr H. Chem. Eur. J. 2010; 16: 11670
27g Palomo C, Oiarbide M, López R. Chem. Soc. Rev. 2009; 38: 632
27h Nair V, Biju AT, Mathew SC, Babu BP. Chem. Asian J. 2008; 3: 810
27i Mukhrjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
27j Janey JM. Angew. Chem. Int. Ed. 2005; 44: 4292
27k Erdik E. Tetrahedron 2004; 60: 8747

28 Qian Z.-Q, Zhou F, Du T.-P, Wang B.-L, Ding M, Zhao X.-L, Zhou J. Chem. Commun. (Cambridge) 2009; 6753
29 Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M. J. Am. Chem. Soc. 2005; 127: 10164
30 Zhou F, Ding M, Liu Y.-L, Wang C.-H, Ji C.-B, Zhang Y.-Y, Zhou J. Adv. Synth. Catal. 2011; 353: 2945
31 Zhou F, Zeng X.-P, Wang C, Zhao X.-L, Zhou J. Chem. Commun. 2013; 49: 2022

For a review, see:

32a Chen L, Yin X.-P, Wang C.-H, Zhou J. Org. Biomol. Chem. 2014; 12: 6033

For our related works, see:

32b Chen L, Zhou F, Shi T.-D, Zhou J. J. Org. Chem. 2012; 77: 4354
32c Chen L, Zhou J. Chem. Asian J. 2012; 7: 2510
32d Chen L, Zhu F, Wang C.-H, Zhou J. RSC Adv. 2013; 3: 19880
32e See also ref. 9l.
32f See also ref. 9i.

33 Zhou F, Ding M, Zhou J. Org. Biomol. Chem. 2012; 10: 3178
34 Yin X.-P, Xu P.-W, Dong K, Liao K, Zhou F, Zhou J. Acta Chim. Sinica 2015; 73: 685

A Journey in the Catalytic Synthesis of 3-Substituted 3-Amino­oxindoles

Authors

A Journey in the Catalytic Synthesis of 3-Substituted 3-Aminooxindoles