4.8 Article

One-pot synthesis of 2H-phenanthro[9,10-c]pyrazoles from isoflavones by two dehydration processes

Journal

GREEN CHEMISTRY
Volume 15, Issue 4, Pages 1048-1054

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3gc40205c

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Funding

  1. National Natural Science Foundation of China [20772076]
  2. Fundamental Funds Research for the Central Universities [Gk200901010]
  3. Innovation Funds of Graduate Programs [2012CXB016]
  4. Shaanxi Normal University [QZZD12064]

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An environmentally friendly and efficient method was developed for one-pot synthesis of a series of 2H-phenanthro[9,10-c]pyrazoles in EtOH by two dehydration processes. Firstly, 3,4-diaryl-1H-pyrazoles were synthesized by the cyclocondensation of isoflavones and hydrazine hydrate in refluxing EtOH. Secondly, the final target products 2H-phenanthro[9,10-c]pyrazoles were given by photocyclization and dehydration of 3,4-diaryl-1H-pyrazoles in 1 : 1 (v/v) EtOH-H2O. The advantages of this method are catalyst-free, short synthetic routes, mild reaction conditions and easy work-up. In addition, the fluorescence properties of 2H-phenanthro[9,10-c]pyrazoles were determined.

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