89617-58-3Relevant academic research and scientific papers
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.
Access to β-lactams by enantioselective palladium(0)-catalyzed C(sp3)-H alkylation
Pedroni, Julia,Boghi, Michele,Saget, Tanguy,Cramer, Nicolai
supporting information, p. 9064 - 9067 (2014/09/17)
β-Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring-opening reactions. Transition-metal-catalyzed C-H functionalizations have emerged as strategy enabling yet uncommon h
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
, 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.
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
, 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.
New 5-nitroimidazoles bearing lactame nucleus: Synthesis and antibacterial properties
Jentzer,Vanelle,Crozet,Maldonado,Barreau
, p. 687 - 697 (2007/10/02)
New 5-nitroimidazoles bearing a trisubstituted ethylenic double bond in position 2 were prepared by reacting various 1-alkyl-2-chloromethyl-5-nitroimidazole with 3-nitrolactam anions by S(RN)1 mechanism in phase-transfer catalysis conditions. These compounds showed in vitro and in vivo antianaerobic activity which was clearly greater than that of metronidazole. Structure-activity relationships have been discussed.
ELECTROREDUCTIVE N-ALKYLATION OF AMIDES, CARBAMATES, AND N-HETEROCYCLES
Shono, Tatsuya,Kashimura, Shigenori,Nogusa, Hideo
, p. 425 - 428 (2007/10/02)
The N-alkylation of amides, lactams, carbamates, and N-heterocycles was easily attained in good yields by the electroreduction of the substrates in the presence of alkyl halides.
Diastereoface-Differentiating Synthesis of Substituted β-Lactams from Chiral Imines and/or Chiral α-Chloro Iminium Chlorides
Rogalska, Ewa,Belzecki, Czeslaw
, p. 1397 - 1402 (2007/10/02)
Reaction of imines carrying a chiral substituent at a nitrogen atom with symmetric or prochiral α-chloro iminium chlorides leads in a diastereoface-differentiating reaction to a mixture of diatereoisomeric or epimeric β-lactams.Attempts were made to determine the absolute configuration of obtained chiral β-lactams.Reaction of prochiral imines with chiral α-chloro iminium chlorides also provides mixtures of diastereomeric β-lactams or their enantiomers with a clear selectivity.
2-Azetidinones from 3-Aminopropanoic Acids and the Ph3P/CCl4(CBr4) or Ph3P/Br2(I2) Condensation Systems
Trifonov, Luchezar S.,Orahovats, Alexander S.
, p. 1117 - 1124 (2007/10/02)
The title complexes are used as intramolecular cyclization agents to yield under mild conditions and average to good yields 2-azetidinones from variously substituted 3-aminopropanoic acids.The reaction is found to proceed in all examined cases stereospeci
