Azonia aromatic heterocycles are an important subclass of aza-heterocyles as they are the structural motif of relevant cationic alkaloids, and they have a wide range of potential applications such as bioactive compounds and organic materials. In this Synopsis, recent and novel approaches to their synthesis are surveyed, with particular emphasis on ring-closing metathesis reactions and annulation reactions based on C-H activation.
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http://dx.doi.org/10.1021/acs.joc.6b01092 | DOI Listing |
J Org Chem
January 2024
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
Cationic aza-heterocycle-fused compounds have gained wide applications in materials science, biological applications, and synthetic organic chemistry. In this report, synthesis of benzothiazolochromenopyridinium tetrafluoroborates, a novel molecular scaffold, bearing 6-6-6-5-6 pentacyclic core is described that proceeds via (i) piperidine-catalyzed Knoevenagel condensation between 2-propargyloxyarylaldehydes bearing internal alkynes and 2-benzothiazoleacetonitrile, (ii) intramolecular formal [4 + 2]-cycloaddition, and (iii) crucial molecular oxygen-mediated oxidative aromatization reaction sequence in one pot. These quaternary pyridinium salts are obtained at ambient temperature in good to high yields.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2024
Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, School of Materials Science and Engineering, Peking University, Beijing, 100871, China.
Conjugated polymers that can efficiently transport both ionic and electronic charges have broad applications in next-generation optoelectronic, bioelectronic, and energy storage devices. To date, almost all the conjugated polymers have hydrophobic backbones, which impedes efficient ion diffusion/transport in aqueous media. Here, we design and synthesize a novel hydrophilic polymer building block, 4a-azonia-naphthalene (AN), drawing inspiration from biological systems.
View Article and Find Full Text PDFCommun Chem
October 2021
Centro de Química Estrutural (CQE) and Institute of Molecular Sciences (IMS), Instituto Superior Técnico, Universidade de Lisboa, 1049-001, Lisboa, Portugal.
Mitochondria metabolism is an emergent target for the development of novel anticancer agents. It is amply recognized that strategies that allow for modulation of mitochondrial function in specific cell populations need to be developed for the therapeutic potential of mitochondria-targeting agents to become a reality in the clinic. In this work, we report dipolar and quadrupolar quinolizinium and benzimidazolium cations that show mitochondria targeting ability and localized light-induced mitochondria damage in live animal cells.
View Article and Find Full Text PDFIUCrdata
April 2021
Department of Chemistry and Physics, Florida Gulf Coast University, 10501 FGCU Blvd. South, Fort Myers, FL, 33965, USA.
Numerous non-covalent inter-actions link together discrete mol-ecules in the crystal structure of the title compound, 2CHNO ·4Cl·HO {systematic name: 4-[(5-ethenyl-1-azonia-bicyclo-[2.2.2]octan-2-yl)(hy-droxy)meth-yl]-6-meth-oxy-quinolin-1-ium dichloride hemihydrate}.
View Article and Find Full Text PDFJ Org Chem
November 2016
Department of Organic and Inorganic Chemistry, University of Alcalá, 28871 Alcalá de Henares, Madrid, Spain.
Azonia aromatic heterocycles are an important subclass of aza-heterocyles as they are the structural motif of relevant cationic alkaloids, and they have a wide range of potential applications such as bioactive compounds and organic materials. In this Synopsis, recent and novel approaches to their synthesis are surveyed, with particular emphasis on ring-closing metathesis reactions and annulation reactions based on C-H activation.
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