79232-58-9Relevant academic research and scientific papers
Taming Radical Pairs in the Crystalline Solid State: Discovery and Total Synthesis of Psychotriadine
Dotson, Jordan J.,Liepuoniute, Ieva,Bachman, J. Logan,Hipwell, Vince M.,Khan, Saeed I.,Houk,Garg, Neil K.,Garcia-Garibay, Miguel A.
, p. 4043 - 4054 (2021/04/06)
Solid-state photodecarbonylation is an attractive but underutilized methodology to forge hindered C-C bonds in complex molecules. This study discloses the use of this reaction to assemble the vicinal quaternary stereocenter motif present in bis(cyclotryptamine) alkaloids. Our strategy was enabled by experimental and computational investigations of the role of substrate conformation on the success or failure of the solid-state photodecarbonylation reaction. This informed a crystal engineering strategy to optimize the key step of the total synthesis. Ultimately, this endeavor culminated in the successful synthesis of the bis(cyclotryptamine) alkaloid "psychotriadine,"which features the elusive piperidinoindoline framework. Psychotriadine, a previously unknown compound, was identified in the extracts of the flower Psychotria colorata, suggesting it is a naturally occurring metabolite.
Diastereoselective synthesis and spin-dependent photodecarbonylation of di(3-phenyl-2-pyrrolidinon-3-yl)ketones: Synthesis of nonadjacent and adjacent stereogenic quaternary centers
Resendiz, Marino J. E.,Natarajan, Arunkumar,Garcia-Garibay, Miguel A.
, p. 193 - 195 (2008/03/12)
A diastereoselective procedure to obtain N-para-methoxybenzyl bis-α,α′-3-(3-phenyl-2-pyrrolidinone)yl substituted ketones with non-adjacent quaternary stereocenters, dl-2 and meso-3 was followed by a photoinduced, spin-dependent, and diastereoselective de
Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomuenchnones
Michael, Joseph P.,De Koning, Charles B.,Van der Westhuyzen, Christiaan W.,Fernandes, Manuel A.
, p. 2055 - 2062 (2007/10/03)
Reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction. However, with 3-substituted piperidine-2-thiones, sulfur was retained in the products, and a range of bicyclic heterocycles, including bicyclic ketene S,N-acetals (2-alkylidene-1,3-thiazolidin-4-ones) and stable thioisomuechnones, was isolated. A novel dimeric ketene S,N-acetal was characterised by X-ray crystallography.
New pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid esters are preferential M1, M3 muscarinic antagonists. Synthesis and bronchospasmolytic activity
Cereda,Ezhaya,Bellora,Schiavi,Sagrada,Doods,Donetti
, p. 411 - 421 (2007/10/02)
A series of new 3-tropanol and 3-quinuclidinol esters of phenyl-substituted pyrrolidin-, piperidin- and azepin-2-oxocarboxylic acid were synthesized and tested for antimuscarinic activity. The compounds showed a preferential in vitro activity at M1 and M3 receptor subtypes and an interesting activity profile in vivo. A potential use as selective bronchospasmolytic agents has been suggested for selected compounds.
Reactions with Aziridines. XXIV: Amidoethylation of Esters of Monosubstituted Malonic Acids
Budny, Jochen,Stamm, Helmut
, p. 657 - 664 (2007/10/02)
Diethyl phenylmalonate (1a) and methylmalonate (1b) have been amidoethylated with the N-acyl aziridines 3a-e under various conditions.In one case only (5) we were able to isolate the primarily formed amidoethyl derivative as minor product which otherwise cyclized apparently completely to form the corresponding N-acyl pyrrolidones 6a-f which mostly underwent further (alcoholytic) reactions.
Reaktionen mit Aziridinen (Aziranen), XXVI. Aminkatalysierte Amidoethylierungen von β-Dicarbonylverbindungen Eine einfache Synthese von 2-Methylpyrrol-1,3-dicarbonester
Stamm, Helmut,Gailius, Viktor
, p. 3599 - 3608 (2007/10/02)
Esters of nonsubstituted and monosubstituted malonic, cyanoacetic, and β-keto acids are easily C-amidoethylated by N-acylaziridines in the presence of triethylamine.In this amine catalyzed reaction the acylaziridines show different degrees of reactivity.Often the products cannot be obtained by the known amidoethylation procedure or but in smaller yields.The new products 3g may smoothly be converted to the pyrroline 9 and further to the 2-methylpyrrole-1,3-dicarboxylate 10. - Divergent from earlier results, the primary amidoethylation product can be isolated from the known sodium salt reaction of tert-butyl acetoacetate with nonbulky acylaziridines.This product is cleaved by trifluoroacetic acid with remarkable easiness to yield the corresponding amidoethyl derivate of acetone.
