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

A Scalable, Combined-Batch, and Continuous-Flow Synthesis of a Bio-Inspired UV-B Absorber

Mark York A C , Karen E. Jarvis A , Jamie A. Freemont A , John H. Ryan A , G. Paul Savage A , Stephanie A. Logan A and Larissa Bright B
+ Author Affiliations
- Author Affiliations

A CSIRO Manufacturing, CSIRO, Clayton, Vic. 3168, Australia.

B Coral Sunscreen Pty Ltd, Aitkenvale, Qld 4814, Australia.

C Corresponding author. Email: mark.york@csiro.au

Australian Journal of Chemistry 72(11) 860-866 https://doi.org/10.1071/CH19252
Submitted: 3 June 2019  Accepted: 5 July 2019   Published: 24 July 2019

Abstract

A new, chromatography-free synthesis for the preparation of an experimental UV-B absorber is reported. A key step of the process is a one-pot partial reduction of a symmetrical imide with a sequential dehydration step. The synthesis uses several continuous-flow steps to increase sample throughput and was used to prepare sufficient material to support further testing activities in >99 % purity.


References

[1]  W. C. Dunlap, J. M. Shick, Y. Yamamoto, Redox Rep. 1999, 4, 301.
         | Crossref | GoogleScholarGoogle Scholar | 10772069PubMed |

[2]  K. Shibata, Plant Cell Physiol. 1969, 10, 325.

[3]  W. C. Dunlap, B. E. Chalker, W. M. Bandaranayake, J. J. Wu Won, Int. J. Cosmet. Sci. 1998, 20, 41.
         | Crossref | GoogleScholarGoogle Scholar | 18505488PubMed |

[4]  R. Losantos, I. Funes-Ardoiz, J. Aguilera, E. Herrera-Ceballos, C. Garcia-Iriepa, P. J. Campos, D. Sampedro, Angew. Chem. Int. Ed. 2017, 56, 2632.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  I. Tsujino, K. Yabe, I. Sekikawa, N. Hamanaka, Tetrahedron Lett. 1978, 19, 1401.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  S. Takano, D. Uemara, Y. Hirata, Tetrahedron Lett. 1978, 19, 2299.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  G. Bird, P. J. Chalmers, N. Fitzmaurice, D. J. Rigg, S. H. Thang, U.S. Patent 5 637 718 1997.

[8]  S. H. Thang, D. J. Rigg, Synth. Commun. 1993, 23, 2355.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  Scifinder commercial sources search April 2019. Available at https://scifinder.cas.org

[10]  M. Tanaka, H. Urata, T. Fuchikami, Tetrahedron Lett. 1986, 27, 3165.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  K. Kondo, T. Takashima, M. Suda, U.S. Patent 4 235 780 1980.

[12]  J. Ryan, M. York, Australian Patent 2013351912 2013.

[13]  G. Kantin, E. Chupakhin, D. Dar’in, M. Krasavin, Tetrahedron Lett. 2017, 58, 3160.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  J. Picha, V. Vanek, M. Budesinsky, J. Mladkova, T. A. Garrow, Eur. J. Med. Chem. 2013, 65, 256.
         | Crossref | GoogleScholarGoogle Scholar | 23727536PubMed |

[15]  H. Flink, T. Putkonen, A. Sipos, R. Jokela, Tetrahedron 2010, 66, 887.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  For a recent review, see: M. B. Plutschack, B. Pieber, K. Gilmore, P. H. Seeberger, Chem. Rev. 2017, 117, 11796.
         | Crossref | GoogleScholarGoogle Scholar | 28570059PubMed |

[17]  Atmospheric Solids Analysis Probe (M&M Mass Spec Consulting LLC: Harbeson, DE). Available at http://www.asap-ms.com/ (accessed 8 July 2019)

[18]  C. Petucci, J. Diffenda, J. Mass Spectrom. 2008, 43, 1565.
         | Crossref | GoogleScholarGoogle Scholar | 18470958PubMed |

[19]  A. D. Ray, J. Hammond, H. Major, Eur. J. Mass Spectrom. 2010, 16, 169.
         | Crossref | GoogleScholarGoogle Scholar |