-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in -xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other -heterocycles, such as acridines, phenoxazines, or phenazines, showcasing the robustness of our technique. In a broader sense, this new method creates two C-N bonds simultaneously based on a mono-halogenated starting material, thus allowing heterocycle formation with diminished halogen waste
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http://dx.doi.org/10.3762/bjoc.20.2 | DOI Listing |
ACS Macro Lett
November 2024
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
Chem Commun (Camb)
October 2024
Xi'an Key Laboratory of Antiviral and Antimicrobial-Resistant Bacteria Therapeutics Research, Xi'an, 710021, China.
An example of palladium/norbornene-catalyzed C-H/N-H cycloaddition of carbazoles with 2-bromobenzoic acids is presented, in which a collection of important carbazoles is expeditiously obtained. Derivatives, including acyl halides, α-oxocarboxylic acids, anhydrides, and even amides, are all allowed. Preliminary mechanistic studies reveal that a rare six-membered spiropalladacycle is involved.
View Article and Find Full Text PDFAntibiotics (Basel)
February 2024
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy, Traian Vuia no. 6, 020956 Bucharest, Romania.
N-acyl hydrazone (NAH) is recognized as a promising framework in drug design due to its versatility, straightforward synthesis, and attractive range of biological activities, including antimicrobial, antitumoral, analgesic, and anti-inflammatory properties. In the global context of increasing resistance of pathogenic bacteria to antibiotics, NAHs represent potential solutions for developing improved treatment alternatives. Therefore, this research introduces six novel derivatives of ()-N'-benzylidene-2-(6-chloro-9-carbazol-2-yl)propanehydrazide, synthesized using a microwave-assisted method.
View Article and Find Full Text PDFJ Org Chem
March 2024
Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana 502 284d, India.
Herein, a straightforward Bro̷nsted acids-promoted domino pathway to build substituted benzo[]carbazoles has been described from easily accessible -formyl (or -acyl) cinnamate esters and indoles. Noticeably, the protocol was amenable to protecting group-free indoles. Notably, this methodology is based on a single-pot regioselective construction of two new C-C bonds and aromatization sequences under mild and metal-free reaction conditions.
View Article and Find Full Text PDFBeilstein J Org Chem
January 2024
Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Straße 7, D-28359 Bremen, Germany.
-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in -xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates.
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