4458-62-2Relevant articles and documents
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.
Harnessing the ortho-directing ability of the azetidine ring for the regioselective and exhaustive functionalization of arenes
Zenzola, Marina,Degennaro, Leonardo,Trinchera, Piera,Carroccia, Laura,Giovine, Arianna,Romanazzi, Giuseppe,Mastrorilli, Piero,Rizzi, Rosanna,Pisano, Luisa,Luisi, Renzo
supporting information, p. 12190 - 12200 (2015/03/31)
This work demonstrates how the directing ability of the azetidine ring could be useful for regioselective ortho-C-H functionalization of aryl compounds. Robust polar organometallic (lithiated) intermediates are involved in this synthetic strategy. The reagent n-hexyllithium emerged as a safer, yet still effective, basic reagent for the hydrogen/lithium permutation relative to the widely used reagent nBuLi. Two different reaction protocols were discovered for regioselective lithiation at the ortho positions adjacent to the azetidine ring, which served as a toolbox when other competing directing groups were installed on the aromatic ring. The coordinating ability of the azetidine nitrogen atom, as well as the involvement of dynamic phenomena related to the preferential conformations of 2-arylazetidine derivatives, were recognized to be responsible for the observed reactivity and regioselectivity. A site-selective functionalization of the aromatic ring was achieved for aryl azetidines with either coordinatively competent groups (e.g. methoxy) or inductively electron-withdrawing substituents (e.g. chlorine and fluorine). By fine-tuning the reaction conditions, regioselective introduction of several substituents on the aromatic ring could be realized. Several substitution patterns were accomplished, which included 1,2,3-trisubstitution, 1,2,3,4-tetrasubstitution, and 1,2,3,4,5-pentasubstitution, up to the exhaustive substitution of the aromatic ring.
N- and C-Silylation of β-lactams
Bergmann,Mayrhofer,Otto
, p. 203 - 216 (2007/10/02)
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