1542817-55-9Relevant academic research and scientific papers
Easy access to constrained peptidomimetics and 2,2-disubstituted azetidines by the unexpected reactivity profile of α-lithiated N-Boc-azetidines
Parisi, Giovanna,Capitanelli, Emanuela,Pierro, Antonella,Romanazzi, Giuseppe,Clarkson, Guy J.,Degennaro, Leonardo,Luisi, Renzo
, p. 15588 - 15591 (2015)
The reactivity profile of lithiated N-Boc-2-arylazetidines has been investigated filling a gap in the chemistry of this class of four-membered heterocycles. Two unexpected and unprecedented results have been observed: an "ortho-effect" accounting for the regioselective functionalization of the azetidine ring, and self-condensation leading to new and interesting azetidine-based peptidomimetics.
Palladium-catalyzed hiyama cross-couplings of arylsilanes with 3-Iodoazetidine: Synthesis of 3-arylazetidines
Liu, Zhenwei,Luan, Nannan,Shen, Linhua,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
supporting information, p. 12358 - 12365 (2019/10/11)
The first palladium-catalyzed Hiyama cross-coupling reactions of arylsilanes with 3-iodoazetidine were described. The protocol provides a convenient access to a variety of useful 3-arylazetidines which are of great interest in pharmaceutical laboratories in moderate to good yields (30%-88%). In addition, this strategy has the advantage of easy operation and mild reaction conditions.
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.
Regioselective functionalization of 2-arylazetidines: Evaluating the ortho-directing ability of the azetidinyl ring and the α-directing ability of the N-substituent
Degennaro, Leonardo,Zenzola, Marina,Trinchera, Piera,Carroccia, Laura,Giovine, Arianna,Romanazzi, Giuseppe,Falcicchio, Aurelia,Luisi, Renzo
supporting information, p. 1698 - 1700 (2014/02/14)
The regioselective lithiation-functionalization of 2-arylazetidines has been explored. The nature of the N-substituent is mainly responsible for a regioselectivity switch. ortho-Lithiation occurred, using hexyllithium as a greener base, in N-alkylazetidines, while α-benzylic lithiation has been observed with N-Boc azetidines.
