37672-46-1Relevant academic research and scientific papers
Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: Applications and mechanism thereof
Balletti, Matteo,De Pedro Beato, Eduardo,Mazzarella, Daniele,Melchiorre, Paolo
, p. 6312 - 6324 (2020/08/24)
We detail a strategy that uses a commercially available nucleophilic organic catalyst to generate acyl and carbamoyl radicals upon activation of the corresponding chlorides and anhydrides via a nucleophilic acyl substitution path. The resulting nucleophilic radicals are then intercepted by a variety of electron-poor olefins in a Giese-type addition process. The chemistry requires low-energy photons (blue LEDs) to activate acyl and carbamoyl radical precursors, which, due to their high reduction potential, are not readily prone to redox-based activation mechanisms. To elucidate the key mechanistic aspects of this catalytic photochemical radical generation strategy, we used a combination of transient absorption spectroscopy investigations, electrochemical studies, quantum yield measurements, and the characterization of key intermediates. We identified a variety of off-the-cycle intermediates that engage in a light-regulated equilibrium with reactive radicals. These regulated equilibriums cooperate to control the overall concentrations of the radicals, contributing to the efficiency of the overall catalytic process and facilitating the turnover of the catalyst. This journal is
CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS
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Paragraph 0293; 0294, (2015/10/28)
The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.
Palladium(II)-Catalyzed Allylic C H Oxidation of Hindered Substrates Featuring Tunable Selectivity Over Extent of Oxidation
Xing, Xiangyou,O'Connor, Nicholas R.,Stoltz, Brian M.
, p. 11186 - 11190 (2016/07/06)
The use of Oxone and a palladium(II) catalyst enables the efficient allylic C H oxidation of sterically hindered α-quaternary lactams which are unreactive under known conditions for similar transformations. This simple, safe, and effective system for C H activation allows for unusual tunable selectivity between a two-electron oxidation to the allylic acetates and a four-electron oxidation to the corresponding enals, with the dominant product depending on the presence or absence of water. The versatile synthetic utility of both the allylic acetate and enal products accessible through this methodology is also demonstrated.
Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3- benzyl-2-piperidinones (δ-valerolactams) and hexahydro-2H-azepin-2-ones (ε- caprolactams)
Reddy, P. Amruta,Woodward, Karen E.,McIlheran, Sarah M.,Hsiang, Bonnie C. H.,Latifi, Tammy N.,Hill, Matthew W.,Rothman, Steven M.,Ferrendelli, James A.,Covey, Douglas F.
, p. 44 - 49 (2007/10/03)
A series of 3-substituted 2-piperidinone (δ-valerolactam) and hexahydro-2H-azepin-2-one (ε-caprolactam) derivatives were prepared and evaluated as anticonvulsants in mice. In the 2-piperidinone series, 3,3- diethyl compound 7b is the most effective antico
PHOTOCYCLIZATION OF ENAMIDES. 38 REDUCTIVE PHOTOCYCLIZATION OF α-(METHYLTHIO)- AND α-(ARYLTHIO)ENAMIDES
Naito, Takeaki,Tanada, Hiromi,Suzuki, Yumiko,Saito, Haruko,Kiguchi, Toshiko,Ninomiya, Ichiya
, p. 2345 - 2366 (2007/10/02)
Reductive photocyclization of α-(methylthio)enamide (2) gave exclusively six-membered lactams (3) and (4) while the same reaction of α-(arylthio)enamides (6) and (12) was found to afford five-membered lactams (7) and (13) as major products.A novel total s
Syntheses of nitrogen heterocycles by means of amine-directed carbonylation and hydrocarbonylation
Zhang, Zhaoda,Ojima, Iwao
, p. 281 - 289 (2007/10/02)
Amine-directed carbonylation of 2-allylpiperidine (5) gives 8-methyl-1-azabicyclononan-9-one (7) with extremely high regio- and stereoselectivity, which is promoted by a stoichiometric amount of 2 in the presence of hydrogen chloride.A c
REDUCTIVE PHOTOCYCLIZATION OF α-METHYLTHIO- AND α-ARYLTHIOENAMIDES
Naito, Takeaki,Tanada, Hiromi,Kiguchi, Toshiko,Ninomiya, Ichiya
, p. 1283 - 1286 (2007/10/02)
Reductive photocyclization of α-methylthio- and α-arylthioenamides (2a-c) gave six-membered lactams (3a-d) and five-membered lactams (4a,b).
Palladium-Catalyzed Carbonylation. A New Synthesis of α-Methylene γ-, δ-, and ε-Lactams and -Lactones Including Bicyclic Lactams of Pyrrolizidine and Indolizidine Skeletons
Mori, Miwako,Washioka, Yumiko,Urayama, Takao,Yoshiura, Kagari,Chiba, Katsumi,Ban, Yoshio
, p. 4058 - 4067 (2007/10/02)
The insertion of carbon monoxide into vinyl halides bearing the secondary amine or alcohol with a catalytic amount of Pd(OAc)2 and PPh3 was realized to give five-, six-, and seven-membered lactams and lactones carrying α-methylene groups in fairly good yields.Bicyclic heterocycles, pyrrolizidine and indolizidine derivatives, were also synthesized from pyrrolidine and piperidine derivatives possessing vinyl halide groups in the side chain at the 2-position of the ring by means of palladium-catalyzed carbonylation.
