Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles*

Hakan Kandemir A B , Ibrahim F. Sengul A C , Naresh Kumar A and David StC. Black A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry, University of New South Wales (UNSW), Sydney, NSW 2052, Australia.

B Department of Chemistry, Faculty of Art and Science, Namık Kemal University, Tekirdag 59100, Turkey.

C Department of Chemistry, Gebze Technical University, PO Box 141, Kocaeli 41400, Turkey.

D Corresponding author. Email: d.black@unsw.edu.au

Australian Journal of Chemistry 70(11) 1196-1201 https://doi.org/10.1071/CH17264
Submitted: 15 May 2017  Accepted: 9 August 2017   Published: 1 September 2017

Abstract

The synthesis of 21-membered imine- and amine-linked tris-indole macrocycles starting from 7-nitroethylindoles is described. The 7-nitroethylindoles are converted to 2,2′-diindolylmethanes and the nitro groups reduced to amino. The resulting diamines undergo reactions with indole-2,7-dicarbaldehydes to form the macrocyclic imines, which can subsequently be reduced to the macrocyclic amines.


References

[1]  X. Yu, D. Sun, Molecules 2013, 18, 6230.
         | CrossRef | 1:CAS:528:DC%2BC3sXpsFemurw%3D&md5=8efd978c0cda789ad4490a6bdb8c2550CAS |

[2]  E. M. Driggers, S. P. Hale, J. Lee, N. K. Terrett, Nat. Rev. Drug Discov. 2008, 7, 608.
         | CrossRef | 1:CAS:528:DC%2BD1cXnvFShsbc%3D&md5=9cd9ab208bd581e60ed494916262f1f4CAS |

[3]  J. Mallinson, I. Collins, Future Med. Chem. 2012, 4, 1409.
         | CrossRef | 1:CAS:528:DC%2BC38XhtFCht7rO&md5=5b40d9206b3bfb3b44bf0cdf534ea522CAS |

[4]  H. C. Zhang, K. B. White, H. Ye, D. F. McComsey, C. K. Derian, M. F. Addo, P. Andrade-Gordon, A. J. Eckardt, B. R. Conway, L. Westover, Bioorg. Med. Chem. Lett. 2003, 13, 3049.
         | CrossRef | 1:CAS:528:DC%2BD3sXms1Gmtr0%3D&md5=94618bfb6f34fd0792251a26b5a2cea3CAS |

[5]  D. StC. Black, N. E. Rothnie, L. C. H. Wong, Aust. J. Chem. 1983, 36, 2407.
         | CrossRef | 1:CAS:528:DyaL2cXhtlWgtbg%3D&md5=af094ccd53431394157849624d565e9fCAS |

[6]  D. StC. Black, D. C. Craig, N. Kumar, L. C. H. Wong, J. Chem. Soc. Chem. Commun. 1985, 1172.
         | CrossRef | 1:CAS:528:DyaL28XhsVSqsrk%3D&md5=8cd8cbc8de8025a4e3670fb904e2e853CAS |

[7]  D. StC. Black, N. Kumar, L. C. H. Wong, Synthesis 1986, 474.
         | CrossRef | 1:CAS:528:DyaL2sXhtF2ktb8%3D&md5=4e48844f11689015b594d560a8ffa7d5CAS |

[8]  P. K. Bowyer, D. StC. Black, D. C. Craig, A. D. Rae, A. C. Willis, J. Chem. Soc., Dalton Trans. 2001, 1948.
         | CrossRef | 1:CAS:528:DC%2BD3MXkslSktrk%3D&md5=75b93d43566774bd19c154a2221bcc5aCAS |

[9]  D. StC. Black, M. C. Bowyer, A. Choy, D. C. Craig, N. Kumar, J. Chem. Soc., Perkin Trans. 1 1989, 200.
         | CrossRef |

[10]  D. StC. Black, Adv. Nitrogen Heterocycl. 1998, 3, 85.
         | CrossRef |

[11]  P. K. Bowyer, D. StC. Black, D. C. Craig, Tetrahedron 2005, 61, 10781.
         | CrossRef | 1:CAS:528:DC%2BD2MXhtVyntLjF&md5=d3077958ae3c7c966da73bc02ec0ae19CAS |

[12]  I. F. Sengul, K. Wood, P. K. Bowyer, M. Bhadbhade, R. Chen, N. Kumar, D. StC. Black, Tetrahedron 2012, 68, 7429.
         | CrossRef | 1:CAS:528:DC%2BC38XhtVCjtL3N&md5=bb9626e18a923dda4453c5292a0b3ca8CAS |

[13]  I. F. Sengul, K. Wood, N. Kumar, D. StC. Black, Tetrahedron 2012, 68, 9050.
         | CrossRef | 1:CAS:528:DC%2BC38Xhtlakt7rL&md5=98e617269a54e1b1d37b7b439195c5e8CAS |

[14]  D. StC. Black, Synlett 1993, 246.
         | CrossRef | 1:CAS:528:DyaK3sXkt1Oqsbw%3D&md5=4ad81ac9d511c2229198bc1aae943ae1CAS |

[15]  H. Sholihin, New Metal Complex Catalysts for Oxidation Reactions 1999, Ph.D. thesis, The University of New South Wales, Sydney, Australia.

[16]  D. StC. Black, in Green Chemistry Series No 1, Collection of Lectures, Summer School on Green Chemistry, 2nd edn (Ed. P. Tundo) 2002, pp. 187–197 (INCA: Mestre, Italy).

[17]  D. StC. Black, in Green Chemistry Series No 1, Collection of Lectures, Summer School on Green Chemistry, 3rd edn (Ed. P. Tundo) 2004, pp. 253–261 (INCA: Mestre, Italy).

[18]  D. StC. Black, in Methods and Reagents for Green Chemistry (Eds P. Tundo, A. Perosa, F. Zecchini) 2007, pp. 219–229 (Wiley: New York, NY).

[19]  D. StC. Black, N. Kumar, L. C. H. Wong, J. Chem. Soc. Chem. Commun. 1985, 1174.
         | CrossRef | 1:CAS:528:DyaL28XhsVSqsrY%3D&md5=294741b31ad4d1f8a813efda417b6da4CAS |

[20]  H. Kandemir, I. F. Sengul, C. R. Gardner, E. L. Werry, M. L. Barron, M. Kassiou, N. Kumar, D. StC. Black, Heterocycles 2016, 93, 333.
         | CrossRef | 1:CAS:528:DC%2BC2sXhtFSht7jF&md5=57797339af6e2f6b3bc61ce66a5f02d7CAS |

[21]  D. StC. Black, M. C. Bowyer, N. Kumar, P. S. R. Mitchell, J. Chem. Soc. Chem. Commun. 1993, 819.
         | CrossRef | 1:CAS:528:DyaK3sXmslWisLc%3D&md5=4cd4eed4f79cffb747e001d15c7b3b09CAS |

[22]  C. Xia, J. Xu, X. Liang, Catal. Commun. 2004, 5, 383.
         | CrossRef | 1:CAS:528:DC%2BD2cXlvVSkurk%3D&md5=17ef58d651d1d6c0c4ddebcadfca443bCAS |

[23]  H. Sajiki, A. Kume, K. Hattori, K. Hirota, Tetrahedron Lett. 2002, 43, 7247.
         | CrossRef | 1:CAS:528:DC%2BD38Xns12isLg%3D&md5=d59c0512b415603183addac8bdb741c2CAS |

[24]  Y. Ukisu, T. Miyadera, J. Mol. Catal. A: Chem. 1997, 125, 135.
         | CrossRef | 1:CAS:528:DyaK2sXntlWgsLc%3D&md5=e197a16ce076c7bc76868c5759fef537CAS |

[25]  A. Furst, R. C. Berlo, S. Hooton, Chem. Rev. 1965, 65, 51.
         | CrossRef | 1:CAS:528:DyaF2MXjs1amtA%3D%3D&md5=fc6bc21e94dc1ac786105dca891f7f07CAS |


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