14278-37-6Relevant articles and documents
Seven-membered rings through metal-free rearrangement mediated by hypervalent iodine
Silva, Siguara Bastos Lemos,Torre, Adriana Della,De Carvalho, Joo Ernesto,Ruiz, Ana Lcia Tasca Gois,Silva, Luiz F.
, p. 1475 - 1494 (2015)
A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) med
Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction
Guney, Tezcan,Wenderski, Todd A.,Boudreau, Matthew W.,Tan, Derek S.
supporting information, p. 13150 - 13157 (2018/09/10)
Medium-ring natural products exhibit diverse biological activities but such scaffolds are underrepresented in probe and drug discovery efforts due to the limitations of classical macrocyclization reactions. We report herein a tandem oxidative dearomatization-ring-expanding rearomatization (ODRE) reaction that generates benzannulated medium-ring lactams directly from simple bicyclic substrates. The reaction accommodates diverse aryl substrates (haloarenes, aryl ethers, aryl amides, heterocycles) and strategic incorporation of a bridgehead alcohol generates a versatile ketone moiety in the products amenable to downstream modifications. Cheminformatic analysis indicates that these medium rings access regions of chemical space that overlap with related natural products and are distinct from synthetic drugs, setting the stage for their use in discovery screening against novel biological targets.
Fluorous bispidine: A bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water
Ang, Wei Jie,Chng, Yong Sheng,Lam, Yulin
, p. 81415 - 81428 (2015/10/06)
Fluorous bispidine-type ligands have been developed to facilitate its recovery and reusability and to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/Knoevenagel condensation in water under mild conditions. Application of the fluorous ligand was also extended to the surfactant-free copper-catalyzed allylic and benzylic sp3 C-H oxidation reaction in water. The fluorous ligands could be recovered using F-SPE with recovery ranging from 91-97% and could be reused five times with little loss of activity.
