Synthesis 2016; 48(18): 3057-3064
DOI: 10.1055/s-0035-1561457
paper
© Georg Thieme Verlag Stuttgart · New York

Three-Component Reaction for the Convenient Synthesis of Functionalized 3-{1-[2-(1H-Indol-3-yl)ethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}indolin-2-ones

Yan-Hong Jiang
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China   eMail: cgyan@yzu.edu.cn
,
Chao-Guo Yan*
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China   eMail: cgyan@yzu.edu.cn
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Publikationsverlauf

Received: 26. Januar 2016

Accepted after revision: 27. April 2016

Publikationsdatum:
07. Juni 2016 (online)


Abstract

A simple synthetic protocol was developed for the efficient synthesis of functionalized 3-{1-[2-(1H-indol-3-yl)ethyl]-4,5,6,7-tetrahydro-1H-indol-3-yl}indolin-2-ones in high yield via three-component reaction of tryptamine, dimedone, and 3-phenacylideneoxindoles in refluxing acetonitrile with p-toluenesulfonic acid as catalyst.

Supporting Information

 
  • References

    • 1a Sundberg RJ. The Chemistry of Indoles . Academic; New York: 1996
    • 1b Santos MM. Tetrahedron 2014; 70: 9735
    • 2a Murray PJ, Kranz M, Ladlow M, Taylor S, Berst F, Holmes AB, Keavey KN, Jaxa-Chamiec A, Seale PW, Stead P. Bioorg. Med. Chem. Lett. 2001; 11: 773
    • 2b Alexander R, Balasundaram A, Batchelor M, Brookings D, Crepy K, Crabbe T, Deltent M.-F, Driessens F, Gill A, Harris S. Bioorg. Med. Chem. Lett. 2008; 18: 4316
    • 2c Zhao M, Bi LR, Wang W, Wang C, Baudy-Floc’h M, Ju JF, Peng SQ. Bioorg. Med. Chem. 2006; 14: 6998
    • 3a Li P, Jiang S, Pero SC, Oligino L, Krag DN, Michejda CJ, Roller PP. Biopolymers 2007; 87: 225
    • 3b Tan ZP, Shang SY, Halkina T, Yuan Y, Danishefsky S. J. Am. Chem. Soc. 2009; 131: 5424
    • 3c Hossany BR, Johnston BD, Wen X, Borrelli S, Yuan Y, Johnson MA, Pinto BM. Carbohydr. Res. 2009; 344: 1412
    • 3d Lin BF, Missirlis D, Krogstad DV, Tirrell M. Biochemistry 2012; 51: 4658
    • 4a Khorana N, Smith C, Herrick-Davis K, Purohit A, Teitler M, Grella B, Dukat M, Glennon RA. J. Med. Chem. 2003; 46: 3930
    • 4b Audia JE, Evrard DA, Murdoch GR, Droste JJ, Nissen JS, Schenck KW, Fludzinski P, Lucaites VL, Nelson DL, Cohen ML. J. Med. Chem. 1996; 39: 2773
    • 4c Kennett GA, Pittaway K, Blackburn TP. Psychopharmacology 1994; 114: 90
    • 5a Yu S, Berner OM, Cook JM. J. Am. Chem. Soc. 2000; 122: 7827
    • 5b Deiters A, Chen K, Eary CT, Martin SF. J. Am. Chem. Soc. 2003; 125: 4541
    • 5c Luo SJ, Zificsak CA, Hsung RP. Org. Lett. 2003; 5: 4809
    • 5d Stork G, Tang PC, Casey M, Goodman B, Toyota M. J. Am. Chem. Soc. 2005; 127: 16255
    • 6a Amat M, Santos MM. M, Bassas O, Llor N, Escolano C, Gomez-Esque A, Molins E, Allin SM, McKee V, Bosch J. J. Org. Chem. 2007; 72: 5193
    • 6b Ma J, Yin WY, Zhou H, Cook JM. Org. Lett. 2007; 9: 3491
    • 6c Dounay AB, Humphreys PG, Overman LE, Wrobleski AD. J. Am. Chem. Soc. 2008; 130: 5368
    • 7a Petea B, Parlagh G. Tetrahedron 2004; 60: 8829
    • 7b Yeo SJ, Liu YX, Wang X. Tetrahedron 2012; 68: 813
    • 7c Neupane P, Li X, Jung JH, Lee YR, Kim SH. Tetrahedron 2012; 68: 2496
    • 7d He Y, Li XL, Li J, Li XC, Guo L, Hai L, Wu Y. Tetrahedron Lett. 2014; 55: 3938
    • 7e Roche SP, Tendoung YJ, Treguier B. Tetrahedron 2015; 71: 3549
    • 8a Bailey PD, Hollinshead SP, Dauter Z. J. Chem. Soc., Chem. Commun. 1985; 1507
    • 8b Bailey PD, Hollinshead SP. Tetrahedron Lett. 1987; 28: 2879
    • 8c Bailey PD, Hollinshead SP. J. Chem. Soc., Perkin Trans. 1 1988; 739
    • 8d Rosenmund P, Brandt B, Flecker P, Hoffmann E. Liebigs Ann. Chem. 1990; 857
    • 8e Rosentreter U, Born L, Kurz J. J. Org. Chem. 1986; 51: 1165
    • 8f Wasserman HH, Frechette R, Oida T, Van Duzer JH. J. Org. Chem. 1989; 54: 6012
    • 8g Bailey PD, Collier ID, Hollinshead SP, Moore MH, Morgan KM, Smith DI, Vernon JM. J. Chem. Soc., Chem. Commun. 1994; 1559
    • 9a Govek SP, Overman LE. J. Am. Chem. Soc. 2001; 123: 9468
    • 9b Condie GC, Bergman J. Eur. J. Org. Chem. 2004; 1286
    • 9c Karpov AS, Rominger F, Mueller TJ. J, Karpov AS. Org. Biomol. Chem. 2005; 3: 4382
    • 9d Chavan SP, Sharma P, Rasapalli S, Kalkote UR. Tetrahedron Lett. 2006; 47: 9301
    • 9e Volz F, Krause N. Org. Biomol. Chem. 2007; 5: 1519
    • 10a Ohba M, Natsutani I, Sakuma T. Tetrahedron 2007; 63: 10337
    • 10b Govek SP, Overman LE. Tetrahedron 2007; 63: 8499
    • 10c Voskressensky LG, Borisova TN, Kulikova LN, Dolgova EG, Kleimenov AI, Sorokina EA, Titov AA, Varlamov AV. Chem. Heterocycl. Compd. 2007; 43: 587
    • 10d Gonzalez-Gomez A, Dominguez G, Perez-Castells J. Tetrahedron 2009; 65: 3378
    • 11a Wu XY, Dai XY, Fang HH, Nie LL, Chen J, Cao WG, Zhao G. Chem. Eur. J. 2011; 17: 10510
    • 11b Dueckert H, Pries V, Khedkar V, Menninger S, Bruss H, Bird AW, Maliga Z, Brockmeyer A, Janning P, Hyman A. Nat. Chem. Bio. 2012; 8: 179
    • 11c Skouta R, Hayano M, Shimada K, Stockwell BR. Bioorg. Med. Chem. Lett. 2012; 22: 5707
    • 11d Chaniyara R, Tala S, Chen CW, Zang XG, Kakadiya R, Lin LF, Chen CH, Chien SI, Chou TC, Tsai TH. J. Med. Chem. 2013; 56: 1544
    • 11e Eschenbrenner-Lux V, Dückert H, Khedkar V, Bruss H, Waldmann H, Frank KV. Chem. Eur. J. 2013; 19: 2294
    • 12a Han Y, Sun Y, Sun J, Yan CG. Tetrahedron 2012; 68: 8256
    • 12b Zhang LL, Sun J, Yan CG. Tetrahedron 2013; 69: 5451
    • 12c Zhu D, Sun J, Yan CG. RSC Adv. 2014; 4: 62817
    • 13a Grimes JH, Angell YM, Kohn WD. Tetrahedron Lett. 2003; 44: 3835
    • 13b Franke PT, Richter B, Jørgensen KA. Chem. Eur. J. 2008; 14: 6317
    • 13c Franzén J, Fisher A. Angew. Chem. Int. Ed. 2009; 48: 787
    • 13d Presset M, Coquerel Y, Rodriguez J. J. Org. Chem. 2009; 74: 415
    • 13e Jin ZC, Wang X, Huang HC, Liang XM, Ye JX. Org. Lett. 2011; 13: 564
    • 14a Rueping M, Sugiono E, Merino E. Chem. Eur. J. 2008; 14: 6329
    • 14b Rueping M, Volla CM. R, Bolte Michael RG. Adv. Synth. Catal. 2011; 353: 2853
    • 14c Neupane P, Li X, Jung JH, Lee YR, Kim SH. Tetrahedron 2012; 68: 2496
    • 14d Ryabukhin SV, Panov DM, Plaskon AS, Tolmachev AA, Smaliy RV. Monatsh. Chem. 2012; 143: 1507
    • 15a Wu XY, Dai XY, Nie LL, Fang HH, Chen J, Ren ZJ, Cao WG, Zhao G. Chem. Commun. 2010; 2733
    • 15b Fang HH, Wu XY, Nie LL, Dai XY, Chen J, Cao WG, Zhao G. Org. Lett. 2010; 12: 5366
    • 15c Dai XY, Wu XY, Fang HH, Nie LL, Chen J, Deng HM, Cao WG, Zhao G. Tetrahedron 2011; 67: 3034
    • 15d Wu XY, Fang HH, Liu Q, Nie LL, Chen J, Cao WG, Zhao G. Tetrahedron 2011; 67: 7251
  • 17 CCDC 1407940 (1k) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
    • 18a Rehn S, Bergman J. Tetrahedron 2005; 61: 3115
    • 18b Shanthi G, Perumal PT. Tetrahedron Lett. 2009; 50: 3959