51-50-3Relevant academic research and scientific papers
Transition Metal-Catalysed Intramolecular Carbenoid C?H Insertion for Pyrrolidine Formation by Decomposition of α-Diazoesters
Solé, Daniel,Amenta, Arianna,Mariani, Francesco,Bennasar, M.-Llu?sa,Fernández, Israel
supporting information, p. 3654 - 3664 (2017/09/13)
The use of Pd-, Rh(II)- and Ru(II)-based catalysts has been explored in the transition metal-catalysed intramolecular carbenoid C?H insertion of α-diazoesters leading to pyrrolidines. Although the outcome of the reaction was highly substrate-dependent, in general, it was possible to control the chemoselectivity of the process towards pyrrolidines by adequate catalyst selection. The Pd(0)-catalysts were as efficient as [Rh(Ph3CCO2)2]2 in promoting the C(sp3)?H insertion of ortho-substituted anilines. In contrast, for anilines bearing meta- and para-substituents, the Rh(II)-catalyst provided the best chemoselectivities and reaction yields. On the other hand, [Ru(p-cymene)Cl2]2 was the most efficient catalyst for the insertion reaction of the N-benzyl-N-phenyl and N,N-dibenzyl α-diazoesters, while the C(sp3)?H insertion of the N-benzylsulfonamide substrate was only promoted by [Rh(Ph3CCO2)2]2. According to density functional theory (DFT) calculations, the mechanism involved in the Pd(0)- and Ru(II)-catalysed C(sp3)?H insertions differs considerably from that typically proposed for the Rh(II)-catalysed transformation. Whereas the Pd(0)-catalysed reaction involves a Pd-mediated 1,5-H migration from the C(sp3)?H bond to the carbenoid carbon atom leading to the formal oxidation of the transition metal, a Ru(II)-promoted Mannich type reaction involving a zwitterionic intermediate seems to be operative in the Ru(II)-catalysed transformation. (Figure presented.).
Synthesis of 2-phenyl- and 2,2-diarylpyrrolidines through Stevens rearrangement performed on azetidinium ions
Drouillat, Bruno,D'Aboville, Edouard,Bourdreux, Flavien,Couty, Francois
supporting information, p. 1103 - 1109 (2014/03/21)
A set of azetidinium ions substituted at the nitrogen atom either by a benzyl group or a benzhydryl group were synthesized to delineate the scope of their ring expansion into 2-phenyl- or 2,2-diaryl-pyrrolidines through a Stevens rearrangement. Whereas th
Synthesis of 2-Phenyl- and 2,2-Diarylpyrrolidines through Stevens Rearrangement Performed on Azetidinium Ions
Drouillat, Bruno,D'Aboville, Edouard,Bourdreux, Flavien,Couty, Fran?ois
supporting information, p. 1103 - 1109 (2015/10/05)
A set of azetidinium ions substituted at the nitrogen atom either by a benzyl group or a benzhydryl group were synthesized to delineate the scope of their ring expansion into 2-phenyl- or 2,2-diaryl-pyrrolidines through a Stevens rearrangement. Whereas th
Mild and efficient capture and functionalisation of CO2 using silver(i) oxide and application to 13C-labelled dialkyl carbonates
Tunbridge, Gemma A.,Baruchello, Riccardo,Caggiano, Lorenzo
, p. 4613 - 4621 (2013/05/08)
A high yielding three-component reaction between β-iodo ethylamine derivatives, MeOH and gaseous CO2 at ambient temperatures and pressures is reported using silver(i) oxide. Unfunctionalised alkyl iodides were also found to be effective in this transformation and their optimisation is also described. To highlight the ease and control with which gaseous CO 2 can be captured and functionalised under mild conditions, the reaction was performed using 13C-enriched CO2 to afford specifically 13C-carbonyl-labelled dialkyl carbonates with exquisite control of the isotopic purity in good yields and without the need for specialised equipment.
Reversal agent and linker variants of reversed chloroquines: Activities against Plasmodium falciparum
Andrews, Simeon,Burgess, Steven J.,Skaalrud, Deborah,Kelly, Jane Xu,Peyton, David H.
supporting information; experimental part, p. 916 - 919 (2010/07/05)
We have shown that "reversed chloroquine molecules" constructed from chloroquine-like and resistance "reversal-agent"-like cores can be powerful drugs against malaria (J. Med. Chem. 2006, 49, 5623-5625). Several reversed chloroquines are now presented that probe parameters governing the activities against chloroquine-resistant and chloroquine-sensitive malaria strains. The design is tolerant to linker and reversal agent changes, but a piperazinyl group adjacent to the quinoline, at least for the group of compounds studied here, may be detrimental. 2009 American Chemical Society.
Improved procedure for the synthesis of enamine N-oxides
Bernier, David,Blake, Alexander J.,Woodward, Simon
, p. 4229 - 4232 (2008/09/20)
(Chemical Equation Presented) An improved procedure for the preparation of enamine N-oxides involving aminolysis of epoxides, chlorination, N-oxidation, and dehydrochlorination is described. Although isolated β-chloroamine N-oxides are prone to rearrangem
Synthesis of novel succinamide derivatives having the 5,11-dihydro-6h- pyrido[2,3-b][1,4]benzodiazepin-6-one skeleton as potent and selective M2 muscarinic receptor antagonists. I
Watanabe, Toshihiro,Kinoyama, Isao,Kakefuda, Akio,Okazaki, Toshio,Takizawa, Kenji,Hirano, Seiko,Shibata, Hiroshi,Yanagisawa, Isao
, p. 996 - 1007 (2007/10/03)
A series of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one derivatives containing the succinamide skeleton has been synthesized and evaluated for M1, M2 and M3 muscarinic receptor binding affinities (in vitro) and M2 and M3 muscarinic receptor antagonistic activities (in vivo). Some of them showed higher and more selective binding affinities for M2 muscarinic receptors than that of AF-DX 116. Among them, 11-[3-[N-[2-(N- benzyl-N-methylamino)ethyl]-N-ethylearbamoyl]propionyl]-5,11-dihydro-6H- pyrido[2,3-b][1,4]benzodiazepin-6-one (68) was found to be the most potent and selective M2 muscarinic receptor antagonist in vitro. This compound also strongly inhibited the oxotremorine-induced bradycardia after intravenous administration and showed 130-fold selectivity for M2 muscarinic receptors over M3 muscarinic receptors in vivo.
