A series of 20 optically pure 3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-ones which form a new family of azaheterocycle-fused [1,3]diazepines were synthesized in four steps with 17-66% overall yields. The key step consists of a selective C-acylation reaction of easily accessible 2-aminoimidazo[1,2-a]pyridine at C-3.
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http://dx.doi.org/10.1021/jo300364d | DOI Listing |
ACS Appl Mater Interfaces
July 2024
Department of Catalysis & Fine Chemicals, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad-500007, India.
Harvesting solar energy to produce value-added chemicals from carbon dioxide (CO) presents a promising route for addressing the complexities of sustainable energy systems and environmental issues. In this context, the development of metal-coordinated porous organic polymers (POPs) offers a vital avenue for improving the photocatalytic performance of organic motifs. The current study presents a metal-integrated photocatalytic system (namely, ) developed via a one-pot Friedel-Crafts (F.
View Article and Find Full Text PDFAcc Chem Res
September 2022
Asymmetric organocatalysis has been considered to be an efficient and reliable strategy for the stereoselective preparation of optically active chemicals. In particular, chiral tertiary amines as Lewis base organocatalysts bearing core structures including quinuclidine, dimethylaminopyridine (DMAP), -methylimidazole (NMI), amidine, etc. have provided new and powerful tools for various chemical transformations.
View Article and Find Full Text PDFAcc Chem Res
April 2021
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Enamine and enol ethers are nucleophilic functional groups that are well known to most chemists. When enamine or enol ethers are present in natural products, they are nearly exclusively found as derivatives having a direct connection to electron-withdrawing groups for stabilization, and the resulting larger entities, such as enamides or enol acylates, can be further extended or modified in the framework of natural products. The restricted conformational space that is associated with even simple enamine and enol ether derivatives can be a strong determinant of the overall molecular structure, and the more polarized derivatives can endow some natural products with electrophilic properties and thus facilitate covalent interactions with biological targets.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
June 2017
ACIB GmbH, Petersgasse 14, 8010, Graz, Austria.
The Friedel-Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel-Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme.
View Article and Find Full Text PDFOrg Lett
October 2016
Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
A general strategy for conjugate addition-C-acylation that enables the synthesis of enantioenriched β-dicarbonyl compounds is described. A novel method for derivatizing these adducts by stereo- and site-selective zinc-catalyzed addition of alkyllithium reagents is also reported. These reactions can be performed in tandem to achieve an enantio- and diastereoselective four-component coupling.
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