85669-65-4Relevant academic research and scientific papers
Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes
Tan, Siu Min,Willis, Anthony C.,Paddon-Row, Michael N.,Sherburn, Michael S.
, p. 3081 - 3085 (2016)
1-Aminodecalins were prepared from acyclic precursors by combining the powerful twofold diene-transmissive Diels-Alder chemistry of [3]dendralenes with the simplicity of enamine formation. On mixing at ambient temperature, a simple dienal condenses with a primary or secondary amine to generate the enamine, a 1-amino-[3]dendralene in situ, and this participates as a double diene in a sequence of two Diels-Alder events with separate dienophiles. Overall, four C-C bonds and one C-N bond are formed. Mechanistic insights into these reactions are provided by means of density functional theory calculations.
One-Step Synthesis of 3,4-Disubstituted 2-Oxazolidinones by Base-Catalyzed CO2 Fixation and Aza-Michael Addition
Mannisto, Jere K.,Sahari, Aleksi,Lagerblom, Kalle,Niemi, Teemu,Nieger, Martin,Sztanó, Gábor,Repo, Timo
supporting information, p. 10284 - 10289 (2019/08/01)
2-Oxazolidinones are saturated heterocyclic compounds, which are highly attractive targets in modern drug design. Herein, we describe a new, single-step approach to 3,4-disubstituted 2-oxazolidinones by aza-Michael addition using CO2 as a carbonyl source and 1,1,3,3-tetramethylguanidine (TMG) as a catalyst. The modular reaction, which occurs between a γ-brominated Michael acceptor, CO2 and an arylamine, aliphatic amine or phenylhydrazine, is performed under mild conditions. The regiospecific reaction displays good yields (av. 75 %) and excellent functional-group compatibility. In addition, late-stage functionalization of drug and drug-like molecules is demonstrated. The experimental results suggest a mechanism consisting of several elementary steps: TMG-assisted carboxylation of aniline; generation of an O-alkyl carbamate; and the final ring-forming step through an intramolecular aza-Michael addition.
Tandem Michael addition and azanorbornane substance-P antagonists
O'Neill,Thadeio,Bundesmann,Elder,McLean,Bryce
, p. 11121 - 11140 (2007/10/03)
Tandem Michael addition product 5 provides a template for azanorbornane derivatives that display potent substance P receptor affinity. The advantages of this synthesis include: the straightforward preparation of both syn and anti azanorbornane diastereomers, access to two, and perhaps more, substituents at C-2 (a and b series), and the straightforward functionalization of the amine at C-3. Mechanistic studies suggest that the second 1,4-addition proceeds kinetically via syn-addition of the nitronate and ester. Conflicting results in the literature stem from a previously unobserved thermodynamic equilibrium which is described herein.
