Weili Zhao

One-Pot Synthesis of Novel Photochromic Oxazine Compounds

A one-pot domino synthesis of photochromic 2,2-diarylphenanthro-(9,10)-[2H]-[1,4]-oxazines in excellent yield is described starting with acrylic acid derivatives. The reaction mechanism was studied by ReactIR and UV-vis. The cascade sequence of the reactions involves five transformations, namely, acyl azide formation, Curtius rearrangement, arsonium ylide formation, aza-Wittig, and final cyclization to the title compounds.

Solid-Phase Synthesis of Photochromic Spiropyrans

[reaction: see text] A convenient solid-phase synthesis of spiropyrans is described. A succinate linker was employed, which allows base-catalyzed cleavage of the desired photochromophore derivatized with a succinimide. Excellent yields and purities were obtained for the compounds that comprise a library of 23 spiropyrans. Opening of the succinimide ring in spiropyran could be realized under mild conditions.