An efficient functional group induced strategy for the synthesis of 6-aminophenanthridines (6AP) has been developed as a result of an in situ generated novel system "CO-CH(N1N2)". This reaction presents a new mode of N2 extrusion in benzotriazoles that later result in decarbonylative cyclization to 6AP. This method offers an easier protocol for the synthesis of 6AP from readily available inexpensive substrates.
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http://dx.doi.org/10.1021/acs.orglett.5b02699 | DOI Listing |
Chem Sci
December 2024
School of Chemistry and Chemical Engineering, Hainan University Haikou 570228 China
The catalytic pyrolysis of guaiacol-based lignin monomers, vanillin, syringol, and eugenol over commercial HZSM-5 has been investigated using Photoelectron Photoion Coincidence (PEPICO) spectroscopy to unveil the reaction mechanism by detecting reactive intermediates, such as quinone methides and ketenes, and products. shares the decomposition mechanism with guaiacol due to prompt and efficient decarbonylation, which allows us to control this reaction leading to a phenol selectivity increase by switching to a faujasite catalyst and decreasing the Si/Al ratio. first demethylates to 3-methoxycatechol, which mainly dehydroxylates to - and -guaiacol.
View Article and Find Full Text PDFChem Commun (Camb)
April 2024
Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
A convenient method for oxidant-promoted radical cascade acylation or decarbonylative alkylation of 1,7-dienes with aldehydes has been established. This method allows for the rapid construction of N-containing polycyclic skeletons in a highly regio- and stereoselective manner. This transformation provides a simple and efficient method for the preparation of a range of tetrahydro-6-indeno[2,1-]quinolinone derivatives by sequential formation of three new carbon-carbon bonds.
View Article and Find Full Text PDFJ Org Chem
April 2024
National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650500, P. R. China.
An unexpected cascade reaction of 2-nitrochalcones with isocyanoacetates has been reported for the efficient synthesis of indole carboxylic esters and pyranoindoles. The conversion was achieved by KOH-catalyzed cyclization and elimination of the nitro group with final decarbonylation-aromatization. The method was used to synthesize a series of potentially biologically active indole derivatives (49 examples) in 67-85% yields under transition-metal-free catalytic conditions.
View Article and Find Full Text PDFCarbohydr Polym
January 2024
Department of Chemistry, College of Chemistry and Materials Science, Panyu Campus, Jinan University, Guangzhou 511443, China. Electronic address:
We fabricated an efficient Pd@HKUST-1@Cu(II)/CMC composite bead catalyst through an innovative strategy based on the unique properties of metal-organic frameworks (MOFs) and carboxymethylcellulose (CMC). In this strategy, HKUST-1 MOFs were grown in-situ on the surface of micrometer-sized Cu-based CMC beads (Cu(II)/CMC), then Pd(II) ions were incorporated into the pores of the MOF and further be partially reduced to Pd(0) NPs, which is an active species for oxidative addition with aryl halides in Sonogashira reactions. The micron-sized Cu(II)/CMC beads were formed through inter/intramolecularly crosslinking facilitated by Cu(II) ions, which was achieved by the metathesis of Cu(II) with numerous carboxylic groups of CMC.
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