4.4 Article

3-(Triflyloxy)benzynes Enable the Regiocontrolled Cycloaddition of Cyclic Ureas to Synthesize 1,4-Benzodiazepine Derivatives

Journal

SYNLETT
Volume 29, Issue 7, Pages 943-+

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1591924

Keywords

benzodiazepines; benzynes; triflyloxy group; imidazolidinones; regioselectivity; directing group

Funding

  1. JSPS KAKENHI [16K08164]
  2. Japanese Agency for Medical Research and Development (AMED) [17am0101084j0001]
  3. Research Foundation for Pharmaceutical Sciences
  4. Kobayashi International Scholarship Foundation
  5. [A16J008680]
  6. Grants-in-Aid for Scientific Research [16K18843, 16J00868, 16K08164, 17KT0010] Funding Source: KAKEN

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A versatile synthesis of 1,4-benzodiazepine derivatives through the reaction of various 3-(trifluoromethanesulfonyloxy)benzynes with N-(p-toluenesulfonyl) imidazolidin-2-ones is reported. This reaction system provides a 1,4-benzodiazepine bearing a trifluoromethanesulfonyloxy group as a single regioisomer among the four possible regioisomers.

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