2315-37-9Relevant articles and documents
Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form γ-lactams
Clarke, Leslie Ann,Ring, Aoife,Ford, Alan,Sinha, Abhijeet S.,Lawrence, Simon E.,Maguire, Anita R.
, p. 7612 - 7628 (2015/02/18)
The first examples of asymmetric copper-catalysed intramolecular C-H insertion reactions of 2-sulfonyl-2-diazoacetamides are described; trans γ-lactams with up to 82% ee are achieved with the CuCl2-bisoxazoline-NaBARF catalyst system. The reactions generally display high efficiency and high trans selectivity, and also a strong regiochemical preference for insertion to lead to the formation of 5-membered rings over 4-membered rings. In cases where there are competing C-H insertion pathways available, to form sulfolanes or thiopyrans, only the insertion into the amide chain to form γ-lactams is observed. With phenylsulfonyl derivatives, a minor competing C-H insertion pathway leading to β-lactams is seen; interestingly, changing the identity of the copper ligand changes the product ratio of β/γ-lactams. The copper catalysed reactions compare favorably in terms of efficiency and enantioselectivity to the corresponding reactions catalysed by commercially available chiral rhodium catalysts.
Synthesis, pharmacology and?molecular modeling of?N-substituted 2-phenyl-indoles and?benzimidazoles as?potent GABAA agonists
Falcó, José Luis,Piqué, Maria,González, Miguel,Buira, Irma,Méndez, Eva,Terencio, Jose,Pérez, Cristina,Príncep, Marta,Palomer, Albert,Guglietta, Antonio
, p. 985 - 990 (2007/10/03)
Among the known non-benzodiazepine hypnotic drugs, Zolpidem (1a), Indiplon (2a) and Zaleplon (2b) have shown high affinity and selectivity for the α1 subunit of the GABA-A receptor. Our group has performed pharmacophoric and ADMET-prediction studies to evaluate a virtual library of new molecules based on privileged structures. Among these, we have synthesized a library of N-substituted indoles and a library of N-substituted benzimidazoles. Afterwards, in vitro screening and in vivo spontaneous motor activity in mice has revealed molecules with good in vitro affinities for the α1 receptor and potent in vivo induction of sedation.
Synthesis of Dibenzocrown Ethers with Pendent Amide Groups
Kasprzyk, Stanislaw P.,Bartsch, Richard A.
, p. 119 - 123 (2007/10/02)
Synthetic routes to twenty six crown ether compounds with pendent amide, N-alkylamide, or N,N-dialkylamide groups are reported.The new crown ether compounds are based on sym-dibenzo-16-crown-5-oxyacetamide and sym-(propyl)-dibenzo-16-crown-5-oxyacetamide and are obtained in high yields.