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

    • Mark York123
    • Adriana Edenharter1
    • 1CSIRO Materials Science and Engineering, Clayton, Vic. 3169, Australia.
    • 2Cooperative Research Centre for Polymers, Notting Hill, Vic. 3168, Australia.
    • 3Advanced Polymerik Pty Ltd, Notting Hill, Vic. 3168, Australia.

    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.

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