40296-20-6Relevant academic research and scientific papers
Efficient synthesis of 3-mono and disubstituted lactams using Meerwein Eschenmoser [3,3] sigmatropic rearrangements
Coates, Brian,Montgomery, David J.,Stevenson, Paul J.
, p. 4025 - 4036 (1994)
3-Allyl substituted five six and seven membered ring lactams, are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser [3,3] rearrangement, using readily available methoxymethyleniminium and lithium alkoxides derived from allyl alcohols.
Diastereoselective heck arylation of spirolactams: An approach to spiroamine-based nicotinic ligands
Kocharit, Chanitsara,Chaiyanurakkul, Arada,Gallagher, Timothy
, p. 3069 - 3072 (2006)
The intermolecular Heck arylations of the cyclopentenyl based spirolactams 6a and 6c are stereoselective leading to adducts 7 and 8 derived by face-selective carbopalladation anti to the lactam carbonyl. Georg Thieme Verlag Stuttgart.
Synthesis of quaternary α-perfluoroalkyl lactams via electrophilic perfluoroalkylation
Katayev,Václavík,Brüning,Commare,Togni
supporting information, p. 4049 - 4052 (2016/03/15)
Efficient protocols enabling the rapid installation of trifluoromethyl, as well as further functionalized fluoroalkyl groups by an electrophilic perfluoroalkylation of lactam-derived ketene silyl amides (KSAs) using hypervalent iodine reagents 1 and 2 have been developed.
Design, synthesis, and cyclization of 4-aminobutyric acid derivatives: Potential candidates as self-immolative spacers
Dewit, Matthew A.,Gillies, Elizabeth R.
experimental part, p. 1846 - 1854 (2011/05/03)
Self-immolative spacers have gained significant interest in recent years due to their utility in numerous prodrug, sensor and drug delivery systems. However, there are a very limited number of spacers that are capable of undergoing spontaneous and rapid reactions under mild conditions. To address this need, 4-aminobutyric acid derivatives were explored as a potential class of self-immolative spacers. Using a modular approach, eleven N- and α-substituted derivatives of 4-aminobutyric acid were synthesized, and their intramolecular cyclizations to γ-lactams were studied. Kinetics experiments were carried out at physiological pH and temperature, and the observed half-lives for the spacers ranged from 2 to 39 s, depending on the molecular structure. In addition, the pH dependence of the cyclization rate was also explored and it was found that cyclization still occurred rapidly at mildly acidic pH. Therefore, this class of compounds exhibits promise for incorporation into a variety of self-immolative systems where rapid cyclization reactions are desired.
Spirocyclic pyridoazepine analogues of galanthamine: Synthesis, modelling studies and evaluation as inhibitors of acetylcholinesterase
Vanlaer, Sofie,De Borggraeve, Wim M.,Voet, Arnout,Gielens, Constant,De Maeyer, Marc,Compernolle, Frans
experimental part, p. 2571 - 2581 (2009/04/06)
Spirocyclic pyridoazepines, designed as simplified analogues of the alkaloid galanthamine, were synthesised and evaluated as inhibitors of acetylcholinesterase. The key cyclisation step involved internal displacement of 2-chloro or 2-iodopyridine by either nucleophilic aromatic substitution or a Heck reaction. The target compounds showed significant inhibition of acetylcholinesterase but lower than that of galanthamine. This result could be rationalised by comparative docking simulation studies based on the known crystal structure of the acetylcholinesterase-galanthamine complex; multiple hydrogen bonding of a cocrystallised water molecule to both the receptor and the ligand was found to be of crucial importance for effective binding to the active site of the enzyme. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis of spirocyclic pyridoazepines as analogues of galanthamine by nucleophilic aromatic substitution of 3-substituted 2-chloropyridines
Vanlaer, Sofie,De Borggraeve, Wim M.,Compernolle, Frans
, p. 4995 - 4998 (2008/03/18)
In this report we describe the synthesis of spirocyclic pyridoazepines starting from easily available precursors. The key step of our synthesis is an intramolecular nucleophilic aromatic substitution of the appropriate 3-substituted 2-chloropyridines. The final compounds, designed as simplified analogues of the alkaloid galanthamine, showed significant acetylcholinesterase inhibition activity. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Preparation of Nitroalkenes: Substitution Reaction via Addition-Elimination Using β-Nitrovinyl Sulfoxides
Nobe, Manabu,Itoh, Akichika,Nishide, Kiyoharu,Abe, Hitoshi,Kawabata, Takeo,et al.
, p. 1119 - 1124 (2007/10/02)
Nitroalkenes were prepared by the substitution reaction of β-nitrovinyl sulfides and sulfoxides with a variety of carbon nucleophiles (i.e. alkylmetal reagents and enolates of carbonyl compounds), via an addition-elimination sequence.The sulfoxide as a leaving group was suitable for the reaction with an enolate of carbonyl compounds.This method was useful for the synthesis of nitroalkenes .
Efficient synthesis of 3-substituted lactams using Meerwein Eschenmoser Claisen [3,3] sigmatropic rearrangements
Coates,Montgomery,Stevenson
, p. 4199 - 4202 (2007/10/02)
3-Allyl substituted five, six and seven membered ring lactams are readily available in good yields and reasonable selectivity by a formal Meerwein Eschenmoser Claisen [3,3] rearrangement, using the readily available N,N-dialkylalkoxymethylene iminium salts and lithium alkoxides derived from allyl alcohols.
-SIGMATROPIC REACTIONS IN THE ENAMINE SERIES
Cervinka, Otakar,Fabryova, Anna,Josef, Jan,Sermek, Vladimir,Smrckova, Svatava
, p. 3407 - 3412 (2007/10/02)
Thermal isomerisation of 1-methyl-2-(3-butenylidene)pyrrolidine (Ib) afforded a mixture of Ib and 1,2-dimethyl-3-allyl-2-pyrroline (IIIa).Analogous reaction with 1-methyl-2-(3-butenyl)-2-piperidine (IIa) gave quantitatively 1,2-dimethyl-3-allyl-2-piperideine (IVa) by -sigmatropic rearrangement.
