Indium trichloride catalyzed three component one-pot route to 1-hydroxymethyl-3-aminomethyl indoles

Tetrahedron Letters

Volumn 53, Issue 41, 2012, Pages 5548-5551

  Acharya, Chiranjit ^a   Dey, Sumit ^a   Jaisankar, Parasuraman ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

1 Hydroxymethyl 3 aminomethyl indoles; Diethyl amine; Formaldehyde; Indium trichloride; Piperidine

Indexed keywords

1 HYDROXYMETHYL 3 AMINOMETHYLINDOLE; DIOXANE; FORMALDEHYDE; INDIUM CHLORIDE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS; ROOM TEMPERATURE;

EID: 84865750447     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.034     Document Type: Article

References (37)

1. For abundance of Indole in natural products, see: T. Eicher, and S. Hauptmann The Chemistry of Heterocycles 2003 Wiley-VCH Weinheim
2. J.A. Joule, and K. Mills Heterocyclic Chemistry 2000 Blackwell Science Ltd. Oxford
3. G.A Cordel Introduction to the Alkaloids 1981 Wiley - Interscience Publication pp. 574
4. D.A. Horton, G.T. Bourne, and M.L. Smythe Chem. Rev. 103 2003 893
5. For antipyretic activity of indole derivatives, see: Foye, Williams O. Principles of Medicinal Chemistry, Fourth edition, 1995, pp. 553.
6. For analgesic activity of indole derivatives, see: N. Pahari, D. Saha, V.K. Jain, B. Jain, and D. Mridha Int. J. Pharma. Sci. Res. 1 2010 399
7. For anticonvulsant activity of indole derivatives, see: H. Rajak, R. Veerasamy, A.K. Gupta, M.D. Kharya, and P. Misra Int. J. Pharma. Sci. Nanotech. 2 2009 661
8. A.E. Shchekotikhin, A.A. Shtill, Y.N. Luzikov, T.V. Bobrysheva, V.N. Buyanov, and M.N. Preobrazhenskaya Bioorg. Med. Chem. Lett. 13 2005 2285
9. For activity of aminomethyl indoles towards PTK, see: Y.G. İşgör, Z. Kiliç, and S. Ölgen Chem. Biol. Drug Des. 72 2008 599
10. For tyrosine kinase, see: S. Ölgen, Y.G. Isgör, and T. Çoban Arch. Pharm. 341 2008 113
11. M. Warmuth, R. Damoiseaux, Y. Liu, D. Fabbro, and N. Gray Curr. Pharm. Des. 9 2003 2043
12. For hemiaminals, see: H.-C. Hsu, and D.-R. Hou Tetrahedron Lett. 50 2009 7169
13. For anti-tumor activity of hemiaminals, see: W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, C. Crogan-Grundy, D. Labreque, M. Bubenick, D. Attardo, R. Denis, S. Lamothe, H. Gourdeau, B. Tseng, S. Kasibhatla, and S.X. Cai J. Med. Chem. 51 2008 417
14. J.-P. Liou, C.-Y. Wu, H.-P. Hsieh, C.-Y. Chang, C.-M. Chen, C.-C. Kuo, and J.-Y. Chang J. Med. Chem. 50 2007 4548
15. For bioavailability of hemiaminals, see: Z. Zhu, H.-G. Chen, O.P. Goel, O.H. Chan, L.A. Stilgenbauer, and B.H. Stewart Bioorg. Med. Chem. Lett. 10 2000 1121
16. H. Bundgaard H. Bundgaard, Design of Prodrugs 1985 Springer Amsterdam pp. 1
17. G. Deguest, L. Bischoff, C. Fruit, and F. Marsais Org. Lett. 9 2007 1165
18. M.B. Smith, and J. March In March's Advanced Organic Chemistry 2007 Wiley-Interscience New York pp. 1281
19. J.A. Chudek, R. Foster, and D. Young J. Chem. Soc., Perkin Trans. 2 1985 1285
20. 3 catalyzed. Diels-Alder reaction, see: G. Babu, and P.T. Perumal Tetrahedron Lett. 38 1997 5025 and references cited therein
21. aldol reaction, see: T.-P. Loh, J. Pei, and M. Lin Chem. Commun. 1996 2315
22. Mannich reactions, see: T.-P. Loh, J. Pei, and G.-Q. Cao Chem. Commun. 1996 1819
23. Fridel-Crafts reactions, see: T.-P. Loh, and L.-L. Wei Tetrahedron Lett. 39 1998 323
24. Various other organic transformations, see: T. Miyai, Y. Onishi, and A. Baba Tetrahedron 1017 1999 55
25. P.R. Krishna, Y.L. Prapurna, and M. Alivelu Tetrahedron Lett. 52 2011 3460 and references cited therein
26. 3 catalyzed organic transformations, see: (a) Singh, M. S.; Raghuvanshi, K. Tetrahedron (in press) http://www.dx.doi.org/10.1016/j.tet.06.099
27. J. Augé, N. Lubin-Germain, and J. Uziel Synthesis 2007 1739
28. B.C. Ranu Eur. J. Org. Chem. 2000 2347 and references cited therein
29. L.R. Reddy, M.A. Reddy, N. Bhanumathi, and K.R. Rao New J. Chem. 25 2001 221
30. 3 catalyst, see: S. Dey, C. Pal, D. Nandi, V.S. Giri, M. Zaidlewicz, M. Krzeminski, L. Smentek, B.A. Hess, J. Gawronski, M. Kwit, N.J. Babu, A. Nangia, and P. Jaisankar Org. Lett. 10 2008 1373
31. S. Dey, D. Nandi, P.K. Pradhan, V.S. Giri, and P. Jaisankar Tetrahedron Lett. 48 2007 2573
32. P.K. Pradhan, S. Dey, V.S. Giri, and P. Jaisankar Synthesis 2005 1779
33. B. Pal, V.S. Giri, and P. Jaisankar Catal. Commun. 6 2005 711
34. S. Sambasiva, and N. Krishnaiyer Chem. Ber. 99 1966 889
35. B.E. Love, and B.T. Nguyen Synlett 1998 1123
36. Shunji, N.; Kazuo, K.; Yasushi, U.; Shinji, M.; Keiichi, M.; Jun, H. WO 19960704, 1996.
37. CCDC number of 3a is 885058. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif. For details see Supplementary data.