2208-05-1Relevant articles and documents
Braude et al.
, (1975)
Cesium Carbonate Catalyzed Esterification of N-Benzyl- N-Boc-amides under Ambient Conditions
Ye, Danfeng,Liu, Zhiyuan,Chen, Hao,Sessler, Jonathan L.,Lei, Chuanhu
supporting information, p. 6888 - 6892 (2019/09/07)
We report a general activated amide to ester transformation catalyzed by Cs2CO3. Using this approach, esterification proceeds under relatively mild conditions and without the need for a transition metal catalyst. This method exhibits broad substrate scope and represents a practical alternative to existing esterification strategies. The synthetic utility of this protocol is demonstrated via the facile synthesis of crown ether derivatives and the late-stage modification of a representative natural product and several sugars in reasonable yields.
Platinum oxide catalyzed silylation of aryl halides with triethylsilane: An efficient synthetic route to functionalized aryltriethylsilanes
Hamze, Abdallah,Provot, Olivier,Alami, Mouad,Brion, Jean-Daniel
, p. 931 - 934 (2007/10/03)
The first platinum-catalyzed selective silylation of aryl halides including aryl iodides and bromides having an electron-withdrawing group is described. The reaction takes place rapidly in NMP with triethylsilane as a silicon source and sodium acetate to provide functionalized aryltriethylsilanes in moderate to good yields. Heteroaromatic halides also were found to be readily silylated with triethylsilane. The procedure is chemoselective and tolerates a wide variety of functional groups.
Design, synthesis, and biological evaluation of substituted benzoate analogues of the selective nicotinic acetylcholine receptor antagonist, methyllycaconitine
Doisy, Xavier,Blagbrough, Ian S.,Wonnacott, Susan,Potter, Barry V. L.
, p. 313 - 317 (2007/10/03)
The norditerpenoid alkaloid methyllycaconitine (MLA) acts as a competitive antagonist on the nicotinic acetylcholine receptor (nAChR) with a high preference for the neuronal α-bungarotoxin (αBgt)-sensitive nAChR over the muscle nAChR in mammals. MLA is thus a useful pharmacological tool. Furthermore, its efficient binding to insect nAChR indicates a high insecticidal potency. Within the complex hexacyclic structure of MLA, we envisaged a potential simple pharmacophore. This led to the design and synthesis of acyclic and monocyclic analogues of MLA. The biological activity of these derivatives at both neuronal nicotinic and muscarinic AChR was evaluated. Some of these structurally simple compounds, despite displaying a modest affinity for the nAChR, showed good specificity. We were able to show the importance of the 2-(methylsuccinimido)benzoate ester moiety and the E-ring of MLA. None of the analogues tested displayed any affinity for [3H]nicotine binding sites in brain membranes, indicating that α7-selectivity is already inherent in these simple structures. If higher affinities are to be obtained, however, there is a clear need for more structural information in the design of second generation simple analogues of MLA.
