14155-36-3Relevant articles and documents
Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C–H Coupling with Oxidatively Sensitive Nucleophiles
Lopez, Marco A.,Buss, Joshua A.,Stahl, Shannon S.
supporting information, p. 597 - 601 (2022/01/20)
Site-selective chlorination of benzylic C–H bonds is achieved using a CuICl/bis(oxazoline) catalyst with N-fluorobenzenesulfonimide as the oxidant and KCl as a chloride source. This method exhibits higher benzylic selectivity, relative to estab
Azetidine-Borane Complexes: Synthesis, Reactivity, and Stereoselective Functionalization
Andresini, Michael,De Angelis, Sonia,Uricchio, Antonella,Visaggio, Angelica,Romanazzi, Giuseppe,Ciriaco, Fulvio,Corriero, Nicola,Degennaro, Leonardo,Luisi, Renzo
, p. 10221 - 10230 (2018/08/01)
The present study reports, for the first time, the synthesis and structural features of azetidine-borane complexes, as well as their reactivity in lithiation reactions. A temperature-dependent stereoselectivity has been disclosed in the reaction of borane with N-alkyl-2-arylazetidines, allowing for a stereoselective preparation of azetidine-borane complexes 2 and 3. A regioselective hydrogen/lithium permutation, at the benzylic position, was observed in lithiation reactions of complexes possessing a syn relationship, between the ring proton and the BH3 group. In contrast, scarce or no reactivity was noticed in complexes lacking such a stereochemical requirement. The configurational stability of the lithiated intermediates has also been investigated, in order to shed some light on the stereoselectivity of the lithiation/electrophile trapping sequence. Calculations helped in supporting experimental observations, concerning structure and reactivity of these azetidine-borane complexes. Data suggest that the BH3 group could promote the lithiation reaction likely by an electrostatic complex induced proximity effect. Interestingly, a new synthetic strategy for the synthesis of N-alkyl-2,2-disubstituted azetidines has been developed.
2-Arylazetidines as ligands for nicotinic acetylcholine receptors
Degennaro, Leonardo,Zenzola, Marina,Laurino, Annunziatina,Cavalluzzi, Maria Maddalena,Franchini, Carlo,Habtemariam, Solomon,Matucci, Rosanna,Luisi, Renzo,Lentini, Giovanni
, p. 329 - 334 (2017/05/17)
Alternative and complementary procedures were adopted for preparing 2-arylazetidine derivatives in moderate to good yields. Preliminary biological evaluation of 2-arylazetidines as ligands of nicotinic acetylcholine receptors allowed to identify chloro-substituted analogs as the most interesting congeners. The title compounds may be considered as suitable hit compounds for developing new nicotinic acetylcholine receptor ligands that may be safer than the currently available drugs targeting nicotinic acetylcholine receptors. Our described synthetic approaches enable facile access to a large number of diversely decorated azetidines for studying the structure-activity relationships and for refining the toxico-pharmacological profile of these agents.
