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

Arthur Lebrêne (1) , Thomas Martzel (1) , Laura Gouriou , Morgane Sanselme , Vincent Levacher (1) , Sylvain Oudeyer (1) , Carlos Afonso (1) , Corinne Loutelier-Bourhis (1) , Jean-François Brière (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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 (KMC) 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 (ESI-IMS-MS) allowing to valid the proposed mechanism.

Domains: Chemical Sciences; Catalysis; Chemical Sciences; Organic chemistry; Chemical Sciences

Arthur Lebrêne, Thomas Martzel, Laura Gouriou, Morgane Sanselme, Vincent Levacher, et al.. The Catalytic Regio- and Stereoselective Synthesis of 1,6-Diazabicyclo[4.3.0]nonane-2,7-diones. Journal of Organic Chemistry, 2021, 86 (13), pp.8600-8609. ⟨10.1021/acs.joc.1c00252⟩. ⟨hal-03322396⟩