4.2 Article

DIHALOGENATIVE CYCLIZATION FOR THE SYNTHESIS OF 4-BROMO-1-BROMOALKYL-5-ARYL/ALKYL/ALKENYL-PYRAZOLES

Journal

HETEROCYCLES
Volume 103, Issue 2, Pages 661-669

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-20-S(K)43

Keywords

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Funding

  1. Hoansha Foundation
  2. Pharmaceutical Society of Japan [N-195302]
  3. [JP18K06590]
  4. [JP19K23815]
  5. [JP19K05467]

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A copper-mediated domino reaction has been developed for the synthesis of 4-bromo-1-bromoalkyl-5-aryl/alkyl/alkenyl-pyrazoles from N,N-disubstituted hydrazones. This method allows for the simultaneous construction of pyrazoles and two C-Br bonds, offering synthetic utility.
A copper-mediated domino reaction involving cyclization, bromination, and nucleophilic substitution of N,N-disubstituted hydrazones, which are labile under oxidative conditions, to synthesize 4-bromo- 1-bromoalkyl-5-aryl/alkyl/alkenyl-pyrazoles, is achieved. This method features the simultaneous construction of pyrazoles and two C-Br bonds, which are synthetically useful.

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