4.8 Article

One-Pot Synthesis of Novel Photochromic Oxazine Compounds

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ORGANIC LETTERS
卷 13, 期 19, 页码 5084-5087

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ol2019482

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资金

  1. National Natural Science Foundation of China [20872026]
  2. Hi-Tech Research and Development Program of China (863 Plan) [2009AA02Z308]
  3. Shanghai Pujiang Talent Plan Project [09PJ01176]
  4. Sino Swiss Science and Technology Cooperation (SSSTC) [EG 30-032010]

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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.

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