A Facile Synthesis of Tris(indolyl)propanes by Concerted 1,2- and 1,4-Friedel-Crafts Attack of Indoles to α,β-Unsaturated Aldimines

Manping Zhao; Xiuli Zhang; Chengxiang He; Pinaki S. Bhadury; Zhihua Sun

doi:10.1071/CH14156

RESEARCH ARTICLE

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A Facile Synthesis of Tris(indolyl)propanes by Concerted 1,2- and 1,4-Friedel-Crafts Attack of Indoles to α,β-Unsaturated Aldimines

Manping Zhao ^A , Xiuli Zhang ^B , Chengxiang He ^A , Pinaki S. Bhadury ^C and Zhihua Sun ^A ^D

+ Author Affiliations

- Author Affiliations

^A College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, 201620, China.

^B School of Fundamental Studies, Shanghai University of Engineering Science, Shanghai, 201620, China.

^C Northernchem Inc., Thorold Stone Road; Niagara Falls, Ontario L2J 1A1, Canada.

^D Corresponding author. Email: sungaris@gmail.com

Australian Journal of Chemistry 68(2) 327-334 https://doi.org/10.1071/CH14156
Submitted: 18 March 2014 Accepted: 9 May 2014 Published: 5 August 2014

Abstract

The Friedel-Crafts reaction of indoles with a wide range of α,β-unsaturated aldimines catalysed by binaphthyl phosphoric acid is demonstrated. The resulting tris(indolyl)propanes are presumably generated by a concerted 1,2- and 1,4-nucleophilic attack to the conjugated imines. According to the preliminary bioassay results, the compound 4e exhibits moderate activity against pancreatic cancer cells.

References

[2] (a) C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjslOnsb0%3D&md5=95e5ca225ab3ee84e916f41e4de16cb3CAS |
      (b) V. Nair, K. G. Abhilash, N. Vidya, Org. Lett. 2005, 7, 5857.
         | Crossref | GoogleScholarGoogle Scholar |

[3] (a) E. Fahy, B. C. M. Potts, D. J. Faulkner, K. Smith, J. Nat. Prod. 1991, 54, 564.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXks1yku74%3D&md5=9049ffda24a41ed38b86e85243c638ceCAS |
      (b) R. Bell, S. Carmeli, N. Sar, J. Nat. Prod. 1994, 57, 1587.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. Bifulco, I. Bruno, R. Riccio, J. Lavayre, G. Bourdy, J. Nat. Prod. 1995, 58, 1254.
         | Crossref | GoogleScholarGoogle Scholar |

[4] (a) K.-H. Lim, O. Hiraku, K. Komiyama, T. Koyano, M. Hayashi, T.-S. Kam, J. Nat. Prod. 2007, 70, 1302.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotlansrs%3D&md5=2cef33deb8a2653eb9589b12252a3a75CAS | 17665953PubMed |
      (b) T. Yamashita, N. Kawai, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2005, 127, 15038.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) X.-H. Cai, Q.-G. Tan, Y.-P. Liu, T. Feng, Z.-Z. Du, W.-Q. Li, X.-D. Luo, Org. Lett. 2008, 10, 577.
         | Crossref | GoogleScholarGoogle Scholar |

[6] R. J. Sundberg, The Chemistry of Indoles 1970 (Academic Press: New York, NY).

[7] (a) J. Bergman, S. Hoegberg, J. Lindstroem, Tetrahedron 1970, 26, 3347.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3cXkslKqtbc%3D&md5=de4a0e4b5a66d59e5929b5555504253eCAS |
      (b) A. Banerjee, A. K. Mukhopadhyay, Indian J. Chem. 1982, 21B, 239.
      (c) D. Chen, L. Yu, P.-G. Wang, Tetrahedron Lett. 1996, 37, 4467.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Denis, H. Mauger, Y. Vallee, Tetrahedron Lett. 1997, 38, 8518.

[9] (a) J. S. Yadav, S. Abraham, B. V. S. Reddy, G. Sabitha, Synthesis 2001, 2165.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXotVSgtLg%3D&md5=f5b35830f8cd72715a71d9b33349de12CAS |
      (b) S.-J. Ji, Synlett 2003, 2074.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S.-Y. Wang, S.-J. Ji, T.-P. Loh, Synlett 2003, 2377.

[10] (a) M. Bandini, P. G. Cozzi, P. Melchiorre, A. Umani-Ronchi, J. Org. Chem. 2002, 67, 5386.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XksFyisbs%3D&md5=937647541f2e9c3f954cb872f0526a33CAS | 12126434PubMed |
      (b) M. Bandini, M. Fagioli, A. Melloni, A. Umani-Ronchi, Adv. Synth. Catal. 2004, 346, 573.
         | Crossref | GoogleScholarGoogle Scholar |

[11] C.-H. Lee, C.-F. Yao, G.-J. Lee-Chen, Y.-C. Wang, Bioformosa 2008, 43, 63.

[14] J. S. Yadav, B. V. S. Reddy, Ch. V. S. R. Murthy, M. Kumar, Ch. Madan, Synthesis 2001, 783.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjt1Wksr4%3D&md5=6d801c726bf852181ff521f68d9c9687CAS |

[15] (a) B. P. Bandgar, K. A. Shaikh, Tetrahedron Lett. 2003, 44, 1959.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtFCnsbg%3D&md5=de8e09ba9970bb61229c0b693671f8b3CAS |
      (b) J. S. Yadav, B. V. S. Reddy, S. Sunitha, Adv. Synth. Catal. 2003, 345, 349.
         | Crossref | GoogleScholarGoogle Scholar |

[16] (a) G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi, P. R. Krishna, Tetrahedron Lett. 2004, 45, 7729.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXns12jsL0%3D&md5=e8b73387a52d648a52a4418a13965a08CAS |
      (b) L. Wang, J. Han, H. Tian, J. Sheng, Z. Fan, X. Tang, Synlett 2005, 337.
         | Crossref | GoogleScholarGoogle Scholar |

[17] B. K. Banik, M. Fernandez, C. Alvarez, Tetrahedron Lett. 2005, 46, 2479.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXit1ylu7Y%3D&md5=782a595a98f8fe3109ed0bce2295e053CAS |

[19] (a) M. Somei, F. Yamada, Nat. Prod. Rep. 2004, 21, 278.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXksFalt7c%3D&md5=c52ee49af2fbca9d50c24809ce4c4923CAS | 15042150PubMed |
      (b) D. J. Faulkner, Nat. Prod. Rep. 2002, 19, 1.
      (c) J. Bosch, M. L. Bennasar, Synlett 1995, 587.
         | Crossref | GoogleScholarGoogle Scholar |

[21] M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. Int. Ed. 2008, 47, 593.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXptFShsg%3D%3D&md5=57593345f0b29a862d51b34089f6a876CAS |

[24] S.-K. Ko, C.-C. Lin, Z.-J. Tu, Y.-F. Wang, C.-C. Wang, C.-F. Yao, Tetrahedron Lett. 2006, 47, 487.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlantLbN&md5=ae7933c36c88b577c9dc31c2459f385fCAS |

[25] J. Jacques, C. Fouquey, Org. Synth. 1989, 67, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXmtFaitr0%3D&md5=1fbcbe71836aee557c92f37c393a6e74CAS |

A Facile Synthesis of Tris(indolyl)propanes by Concerted 1,2- and 1,4-Friedel-Crafts Attack of Indoles to α,β-Unsaturated Aldimines

Abstract

References

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