Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH12435
RESEARCH FRONT
Contents Vol 66(2)

A Two-Stage Continuous-Flow Synthesis of Spirooxazine Photochromic Dyes

Mark York A B C D and Adriana Edenharter A
+ Author Affiliations
- Author Affiliations

A CSIRO Materials Science and Engineering, Clayton, Vic. 3169, Australia.

B Cooperative Research Centre for Polymers, Notting Hill, Vic. 3168, Australia.

C Advanced Polymerik Pty Ltd, Notting Hill, Vic. 3168, Australia.

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

Australian Journal of Chemistry 66(2) 172-177 https://doi.org/10.1071/CH12435
Submitted: 25 September 2012  Accepted: 9 November 2012   Published: 28 November 2012

Abstract

A continuous-flow process for the synthesis of several known and previously unreported spirooxazine photochromic dyes is reported. The process proceeds via an initial copper catalysed addition of substituted anilines to naphthalene-1,2-dione. This is followed by reaction with 1,3,3-trimethyl-2-methyleneindoline in the presence of hydroxylamine hydrochloride to give the desired spirooxazine products. The photochromic dyes were then cast into lenses to allow a preliminary evaluation of their properties.


References

[1]  J. Yoshida, H. Kim, A. Nagaki, ChemSusChem 2011, 4, 331.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjtV2lt7k%3D&md5=f18aa1068233e8c47ef7fd4d50b77bb1CAS |

[2]  D. Webb, T. F. Jamison, Chem. Sci. 2010, 1, 675.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVGrtLs%3D&md5=0a1d1aaeacc075934edc50686b9b69ffCAS |

[3]  J. Wegner, S. Ceylan, A. Kirschning, Chem. Commun. 2011, 47, 4583.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXktF2nsbk%3D&md5=547e0701b180bddbc930bb4f3c07fac7CAS |

[4]  V. Lokshin, A. Samat, A. V. Metelitsa, Russ. Chem. Rev. 2002, 71, 893.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXivVSntLY%3D&md5=a359aa1a23da1b31f0eb648f11de325cCAS |

[5]  H. Bouas-Laurent, H. Durr, Pure Appl. Chem. 2001, 73, 639.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXltVyksrc%3D&md5=5b0c1cb46b71480895b34403a88aeb04CAS |

[6]  N. Malic, J. A. Campbell, A. S Ali, M. York, A. D’Souza, R. A. Evans, Macromolecules 2010, 43, 8488.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFygtrbP&md5=5b26877140088d3be2d3cff6f3d0b8deCAS |

[7]  M. York, R. A. Evans, Tetrahedron Lett. 2010, 51, 2195.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjslSnur8%3D&md5=7f539ddd0b21eab1ff980a74ff00cbe8CAS |

[8]  M. York, Tetrahedron Lett. 2012, 53, 2226.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XjvVWnu78%3D&md5=fceaa2531623cad5727a102069b89509CAS |

[9]  M. York, R. A. Evans, Synth. Commun. 2010, 40, 3618.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtl2ltrzN&md5=08728ea02f7de888e494f31f756a7762CAS |

[10]  D. A. Clarke, B. M. Heron, C. D. Gabbutt, J. D. Hepworth, S. M. Partington, S. N. Corns, U. S. Patent 6 303 673 2001.

[11]  M. Rickwood, S. D. Marsden, V. E. Askew, U. S. Patent 5 446 150 1995.

[12]  A mixture of sodium 1,2-naphthoquinone-4-sulfonate (0.3 g, 1.153 mmol) and N,N,3,5-tetramethylaniline (0.17 g, 1.153 mmol) in 20 % aqueous methanol (8.5 mL) was stirred for 72 h at room temperature. Analysis of the mixture showed none of the desired product had formed.

[13]  Y. Ooyama, T. Okamoto, T. Yamaguchi, T. Suzuki, A. Hayashi, K. Yoshida, Chem. – Eur. J. 2006, 12, 7827.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFKntL7I&md5=0de5f17cb8db245981f6a93a0d980b60CAS |

[14]  Y. Ooyama, S. Nagano, K. Yoshida, Tetrahedron 2009, 65, 1467.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXptl2nuw%3D%3D&md5=0c82f77d5d4549717a63ad023bad25daCAS |

[15]  Y. Ooyama, Y. Kagawa, Y. Harima, Eur. J. Org. Chem. 2007, 3613.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXptVGqtL0%3D&md5=24edb3543fb31e33916d0f8c181dbc71CAS |

[16]  www.vapourtec.co.uk.

[17]  P. R. de Oliveira, D. S. Ribeiro, R. Rittner, J. Phys. Org. Chem. 2005, 18, 513.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXksFylsLs%3D&md5=98505409e0a7cdcc58b81f09cf158897CAS |

[18]  H. Ahlbrecht, E. O. Dueber, J. Epsztajn, R. M. K. Martcinowski, Tetrahedron 1984, 40, 1157.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXkslWrurc%3D&md5=6202ccd0d92723b7c9fddbd7ca4c28e5CAS |