198902-99-7Relevant articles and documents
Intermolecular domino Michael/aldol reactions of α,β-unsaturated esters, aromatic aldehydes, and various nucleophiles promoted with a catalytic amount of a guanidine base in DMSO
Matsuo, Jun-ichi,Morita, Shunya,Yoshimura, Tomoyuki
, (2021/07/28)
In DMSO, a catalytic amount of Barton's base (2-t-butyl-1,1,3,3-tetramethylguanidine, BTMG) effectively catalyzed intermolecular three-component reactions of α,β-unsaturated esters, aldehydes, and carbon-, sulfur-, or nitrogen-pronucleophiles to give three-component addition products with the formation of two new σ-bonds: pronucleophiles and aldehydes reacted with α,β-unsaturated esters at their β-positions and α-positions, respectively. Mechanism studies suggested that these reactions proceeded by the first intermolecular Michael addition of anionic nucleophiles that were formed from pronucleophiles with a catalytic amount of BTMG, followed by intermolecular aldol reactions of transient ester enolates even in the presence of more than stoichiometric amounts of acidic pronucleophiles. High nucleophilicity over Br?nsted basicity of transient enolates in polar solvents was observed for transient ester enolates rather than ketone enolates.
Micellar promiscuity: An expeditious approach to Morita-Baylis-Hillman reaction
Shairgojray, Bashir Ahmad,Dar, Aijaz Ahmad,Bhat, Bilal Ahmad
, p. 2391 - 2394 (2013/06/27)
An accelerated and efficient method for Morita-Baylis-Hillman (MBH) reaction in aqueous cationic micellar solution under ambient conditions has been developed. The present method holds promise for future use of cyclic and acylic MBH-adducts of general uti
Straightforward strategy for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from Baylis-Hillman adducts by 1,3-dipolar cycloaddition and reductive cyclization
Singh, Virender,Singh, Vijay,Batra, Sanjay
scheme or table, p. 5446 - 5460 (2009/05/11)
A straightforward and general approach for the stereoselective synthesis of spiro-fused (C-5)isoxazolino- or (C-3)pyrazolino-(C-3)quinolin-2-ones from the adducts offorded from the Baylis-Hillman reaction of 2-nitrobenzaldehyde and ethyl acrylate by sequential 1,3-dipolar cycloaddition and reductive cyclization is presented. It was found that the reductive cyclization of the isoxazoline derivatives proceeded efficiently in the presence of In/HCl, whereas similar reductions of pyrazolines gave better yields when carried out in the presence of an Fe/AcOH mixture. However, similar attempts employing the Baylis-Hillman adduct of 2-nitrobenzaldehyde and methyl vinyl ketone did not yield the desired compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.