133341-93-2Relevant articles and documents
Directed regioselectiveortho,ortho′-magnesiations of aromatics and heterocycles usingsBu2Mg in toluene
Doerrich, Sabrina B.,Hess, Andreas,Karaghiosoff, Konstantin,Knochel, Paul,Lemaire, Sébastien,Lutter, Ferdinand H.,Prohaska, Jan P.,Trauner, Florian,Wagschal, Simon
, p. 8424 - 8429 (2021)
Aryl azoles are ubiquitous as bioactive compounds and their regioselective functionalization is of utmost synthetic importance. Here, we report the development of a toluene-soluble dialkylmagnesium basesBu2Mg. This new reagent allows mild and regioselectiveortho-magnesiations of variousN-arylated pyrazoles and 1,2,3-triazoles as well as arenes bearing oxazoline, phosphorodiamidate or amide directing groups. The resulting diarylmagnesium reagents were further functionalized either by Pd-catalyzed arylation or by trapping reactions with a broad range of electrophiles (aldehydes, ketones, allylic halides, acyl chlorides, Weinreb amides, aryl halides, hydroxylamine benzoates, terminal alkynes). Furthermore, several doubleortho,ortho′-magnesiations were realized in the case of aryl oxazolines,N-aryl pyrazoles as well as 2-aryl-2H-1,2,3-triazoles by simply repeating the magnesiation/electrophile trapping sequence allowing the preparation of valuable 1,2,3-functionalized arenes.
Assessment of dopamine D1 receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393
Clark, Alia H.,McCorvy, John D.,Watts, Val J.,Nichols, David E.
scheme or table, p. 5420 - 5431 (2011/10/30)
To assess the effect of conformational mobility on receptor activity, the β-phenyl substituent of dopamine D1 agonist ligands of the phenylbenzazepine class, (±)-6,6a,7,8,9,13b-hexahydro-5H-benzo[d] naphtho[2,1-b]azepine-11,12-diol (8), and its oxygen and sulfur bioisosteres 9 and 10, respectively, were synthesized as conformationally-restricted analogs of SKF38393, a dopamine D1-selective partial agonist. Compounds trans-8b, 9, and 10 showed binding affinity comparable to that of SKF38393, but functionally, they displayed only very weak agonist activity. These results suggest that the conformationally-restricted structure of the analogs cannot adopt a binding orientation that is necessary for agonist activity.
Cyclization of aryl acyl radicals generated from S-(4-cyano)phenyl thiolesters by a nickel complex catalyzed electroreduction
Ozaki, Shigeko,Adachi, Masashi,Sekiya, Sayaka,Kamikawa, Rie
, p. 4586 - 4589 (2007/10/03)
Aromatic acyl radicals generated from S-(4-cyano)phenyl 2-alkenylthiobenzoate by a nickel complex catalyzed electroreduction undergo 5- and 6-exo cyclization to give 1-indanone and dihydro-1-naphthalenone derivatives, respectively.
Palladium-mediated ortho-alkylation of 2-aryloxazolines
Clinet, J. C.,Balavoine, G.
, p. C29 - C31 (2007/10/02)
The regioselective ortho-alkylation of 2-aryloxazolines through the reaction of their cyclopalladated complexes with 1-iodoalkanes is described.Depending upon the experimental conditions, either 2- or 2,6-substituted derivatives can be selectively prepare
