Three component tandem reactions involving protected 2-amino indoles, disubstituted propargyl alcohols, and I2/ICl: Iodo-reactant controlled synthesis of dihydro-α-carbolines and α-carbolines via iodo-cyclization/iodo-cycloelimination

Tetrahedron Letters

Volumn 52, Issue 1, 2011, Pages 65-68

  Sharma, Sudhir K ^a   Gupta, Sahaj ^a   Saifuddin, Mohammad ^a   Mandadapu, Anil K ^a   Agarwal, Piyush K ^a   Gauniyal, Harsh M ^a   Kundu, Bijoy ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Carboline; Alkyne; Cyclization; Iodocycloelimination; Multicomponent reaction

Indexed keywords

2 AMINOINDOLE; ALCOHOL DERIVATIVE; CARBOLINE DERIVATIVE; INDOLE DERIVATIVE; IODINE; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ELIMINATION REACTION; ONE POT CONDENSATION; REACTION OPTIMIZATION;

EID: 78649880956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.147     Document Type: Article

References (43)

1. N. Helbecque, C. Moquin, J.L. Bernier, E. Morel, M. Guyot, and J.P. Henichart Cancer Biochem. Biophys. 9 1987 271 279
2. K. Cimanga, T. DeBruyne, L. Pieters, A.J. Vlietinck, and C.A. Turger J. Nat. Prod. 60 1997 688 691
3. B.K.S. Yeung, Y. Nakao, R.B. Kinnel, J.R. Carney, W.Y. Yoshida, and P.J. Scheuer J. Org. Chem. 61 1996 7168 7173
4. J. Kim, K. Shin-ya, K. Furihata, Y. Hayakawa, and H. Seto Tetrahedron Lett. 38 1997 3431 3434
5. H. Raza, R.S. King, R.B. Squires, F.P. Guengerich, D.W. Miller, J.P. Freeman, N.P. Lang, and F.F. Kadlubar Drug Metab. Dispos. 24 1996 395 400
6. A. Jaromin, A. Kozubek, K. Suchoszek-Lukaniuk, M. Malicka-Blaszkiewicz, W. Peczynska-Czoch, and L. Kaczmarek Drug Deliv. 15 2008 49 56
7. N.N. Pogodaeva, V.A. Shagun, and A.A. Semenov Khim.-Fram. Zh. 19 1985 1054 1056
8. W. Peczyska-Czoch, F. Pognan, L. Kaczmarek, and J. Boratynski J. Med. Chem. 37 1994 3503 3510
9. R.K. Bansal, D. Sharma, and J.K. Jain Indian J. Chem. 27 1998 366 367
10. P. Vera-Luque, R. Alajarín, J. Alvarez-Builla, and J.J. Vaquero Org. Lett. 8 2006 415 418
11. S. Hostyn, G.V. Baelen, G.L.F. Lemire, and B.U.W. Maesa Adv. Synth. Catal. 350 2008 2653 2660
12. P. Molina, and P.M. Fresneda Synthesis 1989 878 880
13. E.M. Beccalli, F. Clerici, and A. Marchesini Tetrahedron 57 2001 4787 4792
14. E. Erba, M.L. Gelmi, and D. Pocar Tetrahedron 56 2000 9991 9997
15. A. Ono, and K. Narasaka Chem. Lett. 2001 146 147
16. S. Achab, M. Guyot, and P. Potier Tetrahedron Lett. 36 1995 2615 2618
17. I.T. Forbes, C.N. Johnson, and M. Thompson J. Chem. Soc., Perkin Trans. 1 1992 275 281
18. J.E. Biggs-Houck, A. Younai, and J.T. Shaw Curr. Opin. Chem. Biol. 14 2010 371 382
19. B.B. Tour, and D.G. Hall Chem. Rev. 109 2009 4439 4486
20. J. Lu, X. Gong, H. Yang, and H. Fu Chem. Commun. 2010 4172 4174
21. Y. Zhu, C. Zhai, Y. Yue, L. Yang, and W. Hu Chem. Commun. 2009 1362 1364
22. For review see: L. Weber Drug Discovery Today 7 2002 143 147
23. A. Ulaczyk-Lesanko, and D.G. Hall Curr. Opin. Chem. Biol. 9 2005 266 276
24. P.K. Agarwal, D. Sawant, S. Sharma, and B. Kundu Eur. J. Org. Chem. 2 2009 292 303
25. S. Sharma, and B. Kundu Tetrahedron Lett. 49 2008 7062 7065
26. S.K. Sharma, S. Sharma, P.K. Agarwal, and B. Kundu Eur. J. Org. Chem. 9 2009 1309 1312
27. B. Saha, S. Sharma, D. Sawant, and B. Kundu Tetrahedron Lett. 48 2007 1379 1383
28. B. Saha, R. Kumar, P.R. Maulik, and B. Kundu Tetrahedron Lett. 47 2006 2765 2769
29. D. Sawant, R. Kumar, P.R. Maulik, and B. Kundu Org. Lett. 8 2006 1525 1528
30. S.K. Sharma, A.K. Mandadapu, M. Saifuddin, S. Gupta, P.K. Agarwal, A.K. Mandwal, H.M. Gauniyal, and B. Kundu Tetrahedron Lett. 51 2010 6022 6024
31. S. Ye, K. Gao, and J. Wu Adv. Synth. Catal. 352 2010 1746 1751
32. T. Hino, M. Nakagawa, T. Hashizume, N. Yamaji, and Y. Miwa Tetrahedron Lett. 11 1970 2205 2208
33. M. Nakagawa, H. Yamaguchi, and T. Hino Tetrahedron Lett. 11 1970 4035 4038 and references cited therein
34. S. Roy, and G.W. Gribble Tetrahedron Lett. 48 2007 1003 1005
35. B. Witulski, C. Alayrac, and L. Tevzadze-Saeftel Angew. Chem., Int. Ed. 42 2003 4257 4260
36. R.A. Glennon, and M.V. Strandtmann J. Heterocycl. Chem. 12 1975 135 138
37. See Supplementary data.
38. J. Stykala, J. Slouka, and V. Svecova ARKIVOC 2006 68 75
39. 3 (0.250 g, 1.81 mmol) was added to the reaction mixture at 0 °C and the reaction mixture was allowed to stir at room temperature for 1 h. After completion of the reaction as analyzed by TLC, it was diluted with saturated sodium thiosulphate solution and extracted with EtOAc (20 mL × 3). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product so obtained was purified on a silica gel column using hexane: ethyl acetate (1:9, v/v) as eluent to afford dihydro-α-carbolines 4. General procedure for the one-pot three-component tandem reaction leading to the synthesis of 3-iodo-α-carbolines 5: To a solution of 2-ethoxycarbonylamino-indole-1-carboxylic acid ethyl ester 1a (0.200 g, 0.73 mmol) and 1-(4-chloro-phenyl)-3-phenyl-prop-2-yn-1-ol 2a (0.175 g, 0.73 mmol) in acetonitrile (10 ml), iodine (0.920 g, 3.62 mmol) was added and stirred for 0.5 h at 0 °C to rt. Next, ICl (1 M solution in DCM, 3.4 ml) was added to the reaction mixture at 0 °C and the reaction mixture was allowed to stir at room temperature for 1 h. After completion of the reaction as analyzed by TLC, it was diluted with saturated sodium thiosulphate solution and extracted with EtOAc (20 mL × 3). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product so obtained was purified on a silica gel column using hexane: ethyl acetate (1:19, v/v) as eluent to afford α-carbolines 5.
40. P. Srihari, D.C. Bhunia, P. Sreedhar, S.S. Mandal, J.S.S. Reddy, and J.S. Yadav Tetrahedron Lett. 48 2007 8120 8124
41. E.Y. Akiba Kin-ya, and M. Wada Tetrahedron Lett. 23 1982 429 432
42. P. Forgione, P.D. Wilson, and A.G. Fallis Tetrahedron Lett. 41 2000 17 20
43. R. Mahrwald, S. Quint, and S. Scholtis Tetrahedron Lett. 41 2000 17 20