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Tandem Pd-catalyzed C–C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

Tetrahedron Letters, ISSN: 0040-4039, Vol: 57, Issue: 1, Page: 11-14
2016
  • 23
    Citations
  • 0
    Usage
  • 23
    Captures
  • 0
    Mentions
  • 2
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    23
    • Citation Indexes
      23
  • Captures
    23
  • Social Media
    2
    • Shares, Likes & Comments
      2
      • Facebook
        2

Article Description

The first successful synthesis of 1 H -2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C–C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba) 2 /JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.

Bibliographic Details

Andrey A. Mikhaylov; Alexander D. Dilman; Roman A. Novikov; Yulia A. Khoroshutina; Marina I. Struchkova; Dmitry E. Arkhipov; Yulia V. Nelyubina; Andrey A. Tabolin; Sema L. Ioffe

Elsevier BV

Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry

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