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

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

• 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