The copper-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amines under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. This method allows facile access to polycyclic N-heterocycles with the tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (60-89%).
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http://dx.doi.org/10.1039/d1ob00666e | DOI Listing |
Adv Sci (Weinh)
January 2025
Jihua Hengye Electronic Materials Co. Ltd., Foshan, Guangdong, 528200, P. R. China.
B- and N-heterocyclic fluorophores have reveal promising efficiency in blue organic light-emitting diodes (OLEDs) with small full-width-at-half-maximum (FWHM). However, their structural determinants for spectral broadening and operating stability are still needed to be investigated in further. Herein, a novel multi-N-heterocycles Diindolo[3,2,1jk:3',2',1'jk]dicarbazole[1,2-b:4,5-b] (DIDCz) is proposed to manipulate the emission color toward pure blue region by extending π-conjugation of the N-π-N bridge.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, P. R. China.
A Cu-catalyzed relay process for the preparation of diazidated quinazolinone and polycyclic imidazole derivatives in which readily available alkene-tethered substrates undergo an addition/cyclization/C(sp)-H functionalization of alkene sequences with high efficiency is described. Various functionalized N-heteropolycyclic compounds were readily prepared in good yields with a broad substrate scope. Moreover, the direct azidation of the α-C(sp)-H bond of the corresponding N-heterocycles has been demonstrated on the basis of mechanistic studies, which provide an alternative late-stage functionalization approach for the derivatization of N-heterocyclic scaffolds.
View Article and Find Full Text PDFMolecules
November 2024
Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, College of Chemistry and Life Science, Chengdu Normal University, Chengdu 611130, China.
We report a step-economic strategy for the direct synthesis of novel polycyclic -heterocycle-fused naphthoquinones by merging intramolecular oxidative coupling and cascade [4 + 2] cycloaddition. In the protocol, mechanistic investigations suggest that the cascade reaction involves the intermediate spiro polycyclic -heterocycles and [4 + 2] cycloaddition processes. This protocol is featured with moderate to excellent yields, wide substrate scope, and divergent structures of products.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
State Key Laboratory of New Pharmaceutical Preparations and Excipients, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Materials Science, Hebei Research Center of the Basic Discipline of Synthetic Chemistry, Hebei University, Baoding, Hebei, 071002, P. R. China.
A simple mono/dialkylation of acrylamide derivatives was achieved, affording diverse mono/dialkylated benzo[4,5]imidazo[2,1-]isoquinolines or polycyclic coumarins with good substrate scope. This system used common peroxides as alkylating reagents. Meanwhile, a series of scaled-up reactions and mechanistic explorations well demonstrated the application and reaction process of this cascade system.
View Article and Find Full Text PDFCurr Top Med Chem
August 2024
Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Deanship of Research, Prince Mohammad Bin Fahd University, Al Khobar 31952, Kingdom of Saudi Arabia.
There are many different applications of heterocyclic molecules in the pharmaceutical and materials science fields, which make them an important family of compounds. Among these heterocyclic compounds, nitrogen-containing heterocyclic (N-heterocyclic) compounds have attracted a lot of interest among researchers due to their various applications across a wide variety of fields. Many studies have been performed over the past few years to study the synthesis of N-heterocycles under different reaction conditions, such as solvent-free, catalytic, reactants immobilized on a solid support, one-pot synthesis, and microwave irradiation.
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