Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins

ACS Combinatorial Science

Volumn 14, Issue 4, 2012, Pages 285-293

  MacDonald, Jacob P ^a   Badillo, Joseph J ^a   Arevalo, Gary E ^a   Silva García, Abel ^a   Franz, Annaliese K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

heterocycles; isatins; oxazolines; oxindoles; spiroindolones; spirooxindoles; triazoles

Indexed keywords

ALKYNE; AZIDE; COPPER; INDOLE DERIVATIVE; ISATIN; OXINDOLE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; INDOLES; ISATIN; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84859713750     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300003c     Document Type: Article

References (55)

1. Galliford, C. V.; Scheidt, K. A. Pyrrolidinyl-Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic Agents Angew. Chem., Int. Ed. 2007, 46, 8748-8758 (Pubitemid 350207923)
2. Trost, B. M.; Brennan, M. K. Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products Synthesis 2009, 2009, 3003-3025
3. Badillo, J. J.; Hanhan, N. V.; Franz, A. K. Enantioselective synthesis of substituted oxindoles and spirooxindoles with applications in drug discovery Curr. Opin. Drug Discovery Dev. 2010, 13, 758-776
4. Russel, J. Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization Heterocyclic Scaffolds II; Gribble, G. W., Ed.; Springer: Berlin, 2011; Vol. 26, pp 397-431.
5. Lee, D.; Long, S. A.; Murray, J. H.; Adams, J. L.; Nuttall, M. E.; Nadeau, D. P.; Kikly, K.; Winkler, J. D.; Sung, C.-M.; Ryan, M. D.; Levy, M. A.; Keller, P. M.; DeWolf, W. E. Potent and Selective Nonpeptide Inhibitors of Caspases 3 and 7 J. Med. Chem. 2001, 44, 2015-2026 (Pubitemid 32884524)
6. Abdel-Rahman, A. H.; Keshk, E. M.; Hanna, M. A.; El-Bady, S. M. Synthesis and Evaluation of Some New Spiroindoline-Based Heterocycles As Potentially Active Antimicrobial Agents Biorg. Med. Chem. 2004, 12, 2483-2488 (Pubitemid 38471731)
7. Millemaggi, A.; Taylor, R. J. K. 3-Alkenyl-oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/Telescoped Approaches Eur. J. Org. Chem. 2010, 4527-4547
8. Rottmann, M.; McNamara, C.; Yeung, B. K. S.; Lee, M. C. S.; Zou, B.; Russell, B.; Seitz, P.; Plouffe, D. M.; Dharia, N. V.; Tan, J.; Cohen, S. B.; Spencer, K. R.; González-Páez, G. E.; Lakshminarayana, S. B.; Goh, A.; Suwanarusk, R.; Jegla, T.; Schmitt, E. K.; Beck, H.-P.; Brun, R.; Nosten, F.; Renia, L.; Dartois, V.; Keller, T. H.; Fidock, D. A.; Winzeler, E. A.; Diagana, T. T. Spiroindolones, a Potent Compound Class for the Treatment of Malaria Science 2010, 329, 1175-1180
9. Yeung, B. K. S.; Zou, B.; Rottmann, M.; Lakshminarayana, S. B.; Ang, S. H.; Leong, S. Y.; Tan, J.; Wong, J.; Keller-Maerki, S.; Fischli, C.; Goh, A.; Schmitt, E. K.; Krastel, P.; Francotte, E.; Kuhen, K.; Plouffe, D.; Henson, K.; Wagner, T.; Winzeler, E. A.; Petersen, F.; Brun, R.; Dartois, V.; Diagana, T. T.; Keller, T. H. Spirotetrahydro ß-Carbolines (Spiroindolones): A New Class of Potent and Orally Efficacious Compounds for the Treatment of Malaria J. Med. Chem. 2010, 53, 5155-5164
10. Kamano, Y.; Zhang, H.P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Convolutamydine A, A Novel Bioactive Hydroxyoxindole Alkaloid from Marine Bryozoan Amathia convoluta Tetrahedron Lett. 1995, 36, 2783-2784
11. Cravatto, G.; Giovenzana, G. B.; Palmisano, G.; Pilati, T.; Sisti, M.; Stazi, F. Convolutamydine A: The first authenticated absolute configuration and enantioselective synthesis Tetrahedron: Asymmetry 2006, 17, 3070-3074 (Pubitemid 44969571)
12. Zhou, F.; Liu, Y.-L.; Zhou, J. Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position Adv. Synth. Catal. 2010, 352, 1381-1407
13. Zhou, L.; Liu, Y.; Zhang, W.; Wei, P.; Huang, C.; Pei, J.; Yuan, Y.; Lai, L. Isatin Compounds as Noncovalent SARS Coronavirus 3C-like Protease Inhibitors J. Med. Chem. 2006, 49, 3440-3443 (Pubitemid 43902449)
14. Pibiri, I.; Buscemi, S. A Recent Portrait of Bioactive Triazoles Current Bioactive Compounds 2010, 6, 208-242
15. Tripathi, R. P.; Yadav, A. K.; Ajay, A.; Bisht, S. S.; Chaturvedi, V.; Sinha, S. K. Application of Huisgen (3 + 2) Cycloaddition Reaction: Synthesis of 1-(2,3-Dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and Their Antitubercular Evaluations Eur. J. Med. Chem. 2010, 45, 142-148
16. Siddiqui, N.; Ahsan, W.; Alam, M. S.; Ali, R.; Jain, S.; Azad, B.; Akhtar, J. Triazoles: As Potential Bioactive Agents Int. J. Pharm. Sci. Rev. Res. 2011, 8, 161-169
17. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599 (Pubitemid 34803480)
18. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides J. Org. Chem. 2002, 67, 3057-3064 (Pubitemid 34457265)
19. Meldal, M.; Tornøe, C. W. Cu-Catalyzed Azide-Alkyne Cycloaddition Chem. Rev. 2008, 108, 2952-3015
20. Finn, M. G.; Fokin, V. V. Click Chemistry: Function Follows form Chem. Soc. Rev. 2010, 39, 1231-1232
21. Badillo, J. J.; Arevalo, G. E.; Fettinger, J. C.; Franz, A. K. Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines Org. Lett. 2010, 13, 418-421
22. Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K. Catalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-Oxindoles Angew. Chem., Int. Ed. 2010, 49, 744-747
23. Badillo, J. J.; Silva-García, A.; Shupe, B. H.; Fettinger, J. C.; Franz, A. K. Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones Tetrahedron Lett. 2011, 52 (43) 5550-5553
24. Evans, D. A.; Sweeney, Z. K.; Rovis, T.; Tedrow, J. S. Highly Enantioselective Syntheses of Homopropargylic Alcohols and Dihydrofurans Catalyzed by a Bis(oxazolinyl)pyridine-Scandium Triflate Complex J. Am. Chem. Soc. 2001, 123, 12095-12096 (Pubitemid 33135045)
25. Evans, D. A.; Fandrick, K. R.; Song, H.-J.; Scheidt, K. A.; Xu, R. Enantioselective Friedel-Crafts Alkylations Catalyzed by Bis(oxazolinyl) pyridine-Scandium(III) Triflate Complexes J. Am. Chem. Soc. 2007, 129, 10029-10041 (Pubitemid 47257788)
26. Hanhan, N. V.; Ball-Jones, N. R.; Tran, N. T.; Franz, A. K. Catalytic Asymmetric [3 + 2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles Angew. Chem., Int. Ed. 2012, 51, 989-992
27. Hanhan, N. V.; Tang, Y. C.; Franz, A. K. Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes. Org. Lett. 2012, in press.
28. Taylor, M. S.; Jacobsen, E. N. Highly Enantioselective Catalytic Acyl-Pictet-Spengler Reactions J. Am. Chem. Soc. 2004, 126, 10558-10559 (Pubitemid 39129154)
29. Seayad, J.; Seayad, A. M.; List, B. Catalytic Asymmetric Pictet-Spengler Reaction J. Am. Chem. Soc. 2006, 128, 1086-1087 (Pubitemid 43190615)
30. Stöckigt, J.; Antonchick, A. P.; Wu, F.; Waldmann, H. The Pictet-Spengler Reaction in Nature and in Organic Chemistry Angew. Chem., Int. Ed. 2011, 50, 8538-8564
31. Terada, M. Chiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations Synthesis 2010, 1929-1982
32. Duce, S.; Pesciaioli, F.; Gramigna, L.; Bernardi, L.; Mazzanti, A.; Ricci, A.; Bartoli, G.; Bencivenni, G. An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid-Catalysed Pictet-Spengler Reactions of Isatins Adv. Synth. Catal. 2011, 353, 860-864
33. Kenneth, L, K. Fluorine in Medicinal Chemistry: Recent Therapeutic Applications of Fluorinated Small Molecules J. Fluorine Chem. 2006, 127, 1013-1029
34. Suga, H.; Shi, X.; Fujieda, H.; Ibata, T. Reactions of 5-Alkoxyoxazoles with Aldehydes in the Presence of Lewis Acid: Regio- and Stereoselective Formation of 4-Alkoxycarbonyl-2-oxazolines Tetrahedron Lett. 1991, 32, 6911-6914
35. Suga, H.; Shi, X.; Ibata, T. Regio-Control of Formal [3 + 2] Cycloadditions of 5-Alkoxyoxazoles with Diethyl Oxomalonate Chem. Lett. 1994, 23, 1673-1676
36. Mitchell, J. M.; Shaw, J. T. A Structurally Diverse Library of Polycyclic Lactams Resulting from Systematic Placement of Proximal Functional Groups Angew. Chem., Int. Ed. 2006, 45, 1722-1726 (Pubitemid 44105239)
37. Yu, Z.-X.; Wu, Y.-D. A Theoretical Study of the Mechanisms and Regiochemistry of the Reactions of 5-Alkoxyoxazole with Thioaldehydes, Nitroso Compounds, and Aldehydes J. Org. Chem. 2003, 68, 412-420 (Pubitemid 36125974)
38. Yu, Z.-X.; Wu, Y.-D. A DFT Study of the Mechanisms and Regio- and Stereochemistry of the Lewis Acid-Catalyzed Reactions of 5-Alkoxyoxazoles with Aldehydes: Aryl Substitution at the 2-Position of 5-Alkoxyoxazole Is Critical to the Formation of 4-Alkoxycarbonyl-2-oxazoline J. Org. Chem. 2003, 68, 421-432 (Pubitemid 36125975)
39. Conrad, W. E.; Fukazawa, R.; Haddadin, M. J.; Kurth, M. J. The Davis-Beirut Reaction: N1,N2-Disubstituted-1H-Indazolones via 1,6-Electrophilic Addition to 3-Alkoxy-2H-Indazoles Org. Lett. 2011, 13, 3138-3141
40. Feldman, A. K.; Colasson, B.; Fokin, V. V. One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from In Situ Generated Azides Org. Lett. 2004, 6, 3897-3899 (Pubitemid 39523247)
41. Andersen, J.; Bolvig, S.; Liang, X. Efficient One-Pot Synthesis of 1-Aryl 1,2,3-Triazoles from Aryl Halides and Terminal Alkynes in the Presence of Sodium Azide Synlett 2005, 2941-2947 (Pubitemid 41779609)
42. Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Copper-Catalyzed "Click" Reaction/Direct Arylation Sequence: Modular Syntheses of 1,2,3-Triazoles Org. Lett. 2008, 10, 3081-3084
43. Goddard-Borger, E. D.; Stick, R. V. An Efficient, Inexpensive, and Shelf-Stable Diazotransfer Reagent: Imidazole-1-sulfonyl Azide Hydrochloride Org. Lett. 2007, 9, 3797-3800
44. Nguyen, D. M.; Miles, D. H. Copper(I)-Catalyzed Cycloaddition of Methyl O-Propargylpodocarpate and Azides at Room Temperature Synth. Commun. 2011, 41, 1759-1771
45. Dales, N.; Zhang, Z.; Fonarev, J.; Fu, J.; Kamboj, R.; Kodumuru, V.; Pokrovskaia, N.; Sun, S. Preparation of Thiazole Derivatives As Stearoyl-CoA Desaturase (SCD) Inhibitors. Int. Patent WO2008074835A1, 2008.
46. Guo, C.; Song, J.; Huang, J.-Z.; Chen, P.-H.; Luo, S.-W.; Gong, L.-Z. Core-Structure-Oriented Asymmetric Organocatalytic Substitution of 3-Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)-Folicanthine Angew. Chem., Int. Ed. 2012, 51, 3432-3435
47. Castaldi, M. P.; Troast, D. M.; Porco, J. A. Stereoselective Synthesis of Spirocyclic Oxindoles via Prins Cyclizations Org. Lett. 2009, 11, 3362-3365
48. Campbell-Verduyn, L. S.; Szymanski, W.; Postema, C. P.; Dierckx, R. A.; Elsinga, P. H.; Janssen, D. B.; Feringa, B. L. One-Pot Click reactions: Tandem Enantioselective Biocatalytic Epoxide Ring-Opening and [3 + 2] Azide-alkyne Cycloaddition Chem. Commun. 2010, 46, 898-900
49. Lipinski, C. A. Lead- and Drug-like Compounds: The Rule-of-Five Revolution Drug Discovery Today: Technologies 2004, 1, 337-341 (Pubitemid 40186335)
50. Hann, M. M.; Oprea, T. I. Pursuing the leadlikeness concept in pharmaceutical research Curr. Opin. Chem. Biol. 2004, 8, 255-263 (Pubitemid 38759400)
51. Wang, R.; Fu, Y.; Lai, L. A New Atom-Additive Method for Calculating Partition Coefficients J. Chem. Inf. Comput. Sci. 1997, 37, 615-621 (Pubitemid 127603572)
52. Arkin, M. R.; Wells, J. A. Small-molecule Inhibitors of Protein-protein Interactions: Progressing Towards the Dream Nat. Rev. Drug Discovery 2004, 3, 301-317 (Pubitemid 38499758)
53. Yin, H.; Hamilton, A. D. Strategies for Targeting Protein-Protein Interactions with Synthetic Agents Angew. Chem., Int. Ed. 2005, 44, 4130-4163 (Pubitemid 40982718)
54. Sauer, W. H. B.; Schwarz, M. K. Molecular Shape Diversity of Combinatorial Libraries: A Prerequisite for Broad Bioactivity J. Chem. Inf. Comput. Sci. 2003, 43, 987-1003
55. Ertl, P.; Rohde, B.; Selzer, P. Fast Calculation of Molecular Polar Surface Area as a Sum of Fragment Based Contributions and its Application to the Prediction of Drug Transport Properties J. Med. Chem. 2000, 43, 3714-3717