4.7 Article

The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 13, Pages 8600-8609

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00252

Keywords

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Funding

  1. INSA Rouen Normandy
  2. University of Rouen Normandy
  3. Centre National de la Recherche Scientifique (CNRS)
  4. EFRD
  5. Labex SynOrg [ANR-11-LABX-0029]
  6. Region Normandie (CRUNCh network)
  7. French National Research Agency (ANR) [ANR-16-CE07-0011-01]
  8. Agence Nationale de la Recherche (ANR) [ANR-16-CE07-0011] Funding Source: Agence Nationale de la Recherche (ANR)

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A straightforward method for synthesizing original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was developed using a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction. Analysis of key reactive intermediates using mass spectrometry confirmed the proposed mechanism.
A straightforward synthesis of original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was achieved through a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction which takes advantage of an unprecedented highly regio- and diastereoselective conjugate addition of pyridazinones to alkylidene Meldrum's acid intermediates. The key reactive intermediates of this complex process were analyzed by means of electrospray ionization mass spectrometry coupled to ion mobility spectrometry, allowing us to validate the proposed mechanism.

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