Preparation of polyfunctional aryl azides from aryl triazenes. A new synthesis of ellipticine, 9-methoxyellipticine, isoellipticine, and 7-carbethoxyisoellipticine.

No abstract is available for this paper.

• Publication year

  2007

• Venue

  Journal of Organic Chemistry

• Publication date

  2007-08-18

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/JO070774ZPMID 17705535
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Magnesiated unsaturated silylated cyanohydrins as synthetic equivalents of aromatic and heterocyclic grignard reagents bearing a ketone or an aldehyde.

  2006cited by this paper
• Preparation of polyfunctional arylmagnesium reagents bearing a triazene moiety. A new carbazole synthesis.

  2005cited by this paper
• Preparation of cyclic alkenylmagnesium reagents via an iodine/magnesium exchange.

  2005cited by this paper
• Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions.

  2005cited by this paper
• Stepwise and directional synthesis of end-functionalized single-oligomer OPVs and their application in organic solar cells.

  2004cited by this paper
• Stereoselective preparation of functionalized acyclic alkenylmagnesium reagents using i-PrMgCl.LiCl.

  2004cited by this paper
• Convenient magnesiation of aromatic and heterocyclic rings bearing a hydroxy group in presence of LiCl.

  2004cited by this paper
• A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides.

  2004cited by this paper
• Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity.

  2003cited by this paper
• En route to surface-bound electric field-driven molecular motors.

  2003cited by this paper
• Highly functionalized organomagnesium reagents prepared through halogen-metal exchange.

  2003cited by this paper
• Isolation and synthesis of biologically active carbazole alkaloids.

  2002cited by this paper
• m-Diethynylbenzene macrocycles: syntheses and self-association behavior in solution.

  2002cited by this paper
• Metabolism and disposition studies of 9-hydroxyellipticine and 2-methyl-9-hydroxyellipticinium acetate in animals.

  1980cited by this paper
• Methoxy-9-ellipticine lactate. 3. Clinical screening: its action in acute myeloblastic leukaemia.

  1970cited by this paper

• Metal-free para-selective C-H amination and azidation of N-arylhydroxylamines

  2025cites this paper
• A critical review on rubriflordilactones A, B, and C: occurrence, structural diversity, bioactivities, and synthesis.

  2025cites this paper
• 1,2-Bis-Triazenylarenes Enable Vicinal Sandmeyer-Type Reactions.

  2025cites this paper
• Photoirradiation-Promoted ipso-Azidation of 1-Aryltriazenes.

  2025cites this paper
• Development of 3-triazenylaryne and its application to iterative aryne reactions via o-triazenylarylboronic acids.

  2023cites this paper
• Synthesis and evaluation of potent (iso)ellipticine-based inhibitors of MYLK4 accessed via expeditious synthesis from isoquinolin-5-ol

  2023cites this paper
• Covalent Association of a Ruthenium‐Based Chromophore and a Copper Catalyst: A Synergy for Sulfides Photo‐oxidation

  2023cites this paper
• Synthesis of Multisubstituted Aromatics via 3-Triazenylarynes.

  2023cites this paper
• A DDQ-mediated ring-opening and aromatization cascade of a tetrahydrocarbazole-fused tetrahydrofuran for the synthesis of olivacine

  2023cites this paper
• Synthesis, Biological Activity and Photophysical Studies of Ellipticine and its Derivatives: State of the Art

  2022cites this paper
• Microwave and Ultrasonic‐Assisted Synthesis of Highly Functionalized Carbazoles And Dibenzofurans from Biaryl‐Triazenes Promoted by Acidic Ionic Liquid

  2022cites this paper
• Synthesis of Four-Membered BN3 Heterocycles by the Borylation of Triazenes.

  2022cites this paper
• Exploiting an intramolecular Diels-Alder cyclization/dehydro-aromatization sequence for the total syntheses of ellipticines and calothrixin B.

  2021cites this paper
• Synthesis of N-arylacetamides via amination of aryltriazenes with acetonitrile under metal-free and mild conditions

  2021cites this paper
• Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications.

  2020cites this paper
• Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes.

  2019cites this paper
• A fluorogenic C4N4 probe for azide-based labelling.

  2019cites this paper
• Metal-Free C-H Functionalization and Aromatization Sequence for the Synthesis of 1-(Indol-3-yl)carbazoles and Total Synthesis of 7-Bromo-1-(6-bromo-1 H-indol-3-yl)-9 H-carbazole.

  2019cites this paper
• Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade.

  2019cites this paper
• Synthesis of Heteroaryl Triazenes via Rh(III)‐catalyzed Annulation Reactions with Alkynyl Triazenes

  2019cites this paper
• Mild and Efficient Synthesis of Functionalized Carbazoles via a DBU‐Assisted Sequence Involving Cu‐ and Pd‐Catalyzed Coupling Reactions

  2019cites this paper
• Ellipticine, its Derivatives: Re-Evaluation of Clinical Suitability with the Aid of Drug Delivery Systems.

  2019cites this paper
• Ionic liquid-mediated synthesis and functionalization of heterocyclic compounds

  2019cites this paper
• Divergent Synthesis of Densely Substituted Arenes and Pyridines via Cyclotrimerization Reactions of Alkynyl Triazenes.

  2019cites this paper
• A transition metal-free approach to a regioselective total synthesis of the natural product derivative 6-methylellipticine, a potent anticancer agent

  2019cites this paper
• An environmentally friendly approach to the green synthesis of azo dyes with aryltriazenes via ionic liquid promoted C-N bonds formation

  2018cites this paper
• Mild Dirhodium(II)-Catalyzed Chemo- and Regioselective Azidation of Arenes.

  2018cites this paper
• Rh(iii)-Catalyzed dual C-H functionalization of 3-(1H-indol-3-yl)-3-oxopropanenitriles with sulfoxonium ylides or diazo compounds toward polysubstituted carbazoles.

  2018cites this paper
• Determination of binding modes and binding constants for the complexes of 6H-pyrido[4,3-b]carbazole derivatives with DNA.

  2017cites this paper
• Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

  2017cites this paper
• Unprecedented Cyclic Isomer of Triazenes: A Computational Identification

  2017cites this paper
• Divergent Asymmetric Synthesis of Polycyclic Compounds via Vinyl Triazenes.

  2017cites this paper
• Regioselective synthesis of 2,3'-biindoles mediated by an NBS-induced homo-coupling of indoles.

  2017cites this paper
• N-Bromosuccinimide (NBS)-Catalyzed C-H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles.

  2017cites this paper
• Cross-Dehydrogenative Coupling (CDC) as Key-Transformations to Various D-π-A Organic Dyes: C-H/C-H Synthetic Study Directed toward Dye-Sensitized Solar Cells Applications.

  2017cites this paper
• Boron trifluoride etherate

  2017cites this paper
• Highly Efficient Brønsted Acidic Ionic Liquid Promoted Direct Diazenylation of Pyrazolones with Aryltriazenes under Mild Conditions

  2017cites this paper
• Synthesis and cytotoxic activity of novel 11-methyl-6H-pyrido[4,3-b]carbazole derivatives linked to amine, N-methylurea, and N-methyl-N-nitrosourea moieties with various types of carbamoyl tethers at the C-5 atom

  2016cites this paper
• Concise Total Syntheses of Pyr­ido[4,3‐b]carbazole Alkaloids Using Copper‐Mediated 6π‐Electrocyclization

  2016cites this paper
• Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions.

  2016cites this paper
• Synthetic Study of Rubriflordilactone B: Highly Stereoselective Construction of the C-5-epi ABCDE Ring System.

  2016cites this paper
• Nickel‐Catalyzed C(Aryl)−O Bond Activation/Cross‐Coupling Reaction of Carbazoles with Methyl Grignard: Synthesis of Ellipticine

  2016cites this paper
• 27. Sundberg Indole Synthesis

  2016cites this paper
• Synthesis of Tetracyclic Tetrahydro‐β‐carbolines by Acid‐Promoted One‐Pot Sequential Formation of C−C and C−N Bonds

  2016cites this paper
• Protected Diazonium Salts: A Continuous-Flow Preparation of Triazenes Including the Anticancer Compounds Dacarbazine and Mitozolomide

  2016cites this paper
• Carbon-Carbon Sigma Bond Activation: Functionalizing C-C and C-CN Bonds via Carboacylation and Cyanoamidation

  2015cites this paper
• Progress and developments in the turbo Grignard reagent i-PrMgCl·LiCl: a ten-year journey.

  2015cites this paper
• Selective Protection of Secondary Amines as the N-Phenyltriazenes. Application to Aminoglycoside Antibiotics.

  2015cites this paper
• Palladium-catalyzed direct C2 arylation of N-substituted indoles with 1-aryltriazenes.

  2014cites this paper
• Sc(OTf)3-catalyzed transfer diazenylation of 1,3-dicarbonyls with triazenes via N-N bond cleavage.

  2014cites this paper
• Progress in Silver-Mediated/Catalyzed Trifluoromethylation

  2014cites this paper
• Azides – Diazonium Ions – Triazenes: Versatile Nitrogen-rich Functional Groups

  2014cites this paper
• Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives.

  2014cites this paper
• Synthesis and complexation study of new ExTTF-based hosts for fullerenes.

  2014cites this paper
• Single-crystal Cultivation and Structure Analysis of Unstable 1-Azido-2-chloro-4-nitrobenzene

  2014cites this paper
• Total Synthesis of Dictyodendrins B and E, and Formal Synthesis of Dictyodendrin C

  2014cites this paper
• Silver-mediated methoxycarbonyltetrafluoroethylation of arenes.

  2013cites this paper
• ortho-Perfluoroalkylation and ethoxycarbonyldifluoromethylation of aromatic triazenes.

  2013cites this paper
• Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: selective synthesis of benzo-fused azole derivatives.

  2013cites this paper
• Reactions of arynes with nitrosoarenes--an approach to substituted carbazoles.

  2013cites this paper
• Evaluation of Green Corrosion Inhibition by Alkaloid Extracts of Ochrosia oppositifolia and Isoreserpiline against Mild Steel in 1 M HCl Medium

  2013cites this paper
• BF3·OEt2-Promoted Intramolecular Nucleophilic Substitution; Synthesis of Dibenzopyranones and Coumarins from Biaryltriazenes

  2013cites this paper
• Reaktionen von Arinen mit Nitrosoarenen – ein Zugang zu substituierten Carbazolen

  2013cites this paper
• Isolation, biological activity and synthesis of the natural product ellipticine and related pyridocarbazoles

  2012cites this paper
• Ortho‐Trifluormethylierung funktionalisierter aromatischer Triazene

  2012cites this paper
• Copper-catalyzed C-H azidation of anilines under mild conditions.

  2012cites this paper
• Fluorogenic azidofluoresceins for biological imaging.

  2012cites this paper
• Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids.

  2012cites this paper
• Convenient Approaches towards the Synthesis of Novel Pyrano[2,3‐a]carbazoles

  2012cites this paper
• Ortho-trifluoromethylation of functionalized aromatic triazenes.

  2012cites this paper
• Lewis‐Acid‐Promoted Arylation Reaction: Synthesis of Dihydrobenzofuran Derivatives from Aryltriazenes

  2012cites this paper
• Ellipticines and 9-acridinylamines as inhibitors of D-alanine:D-alanine ligase.

  2011cites this paper
• Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence

  2011cites this paper
• Iron-catalyzed bromination of aryl azides by N-bromosuccinimide: Efficient method for the synthesis of brominated aryl azides

  2011cites this paper
• Synthesis of carbazoles and 1,2-dihydrocarbazoles by domino ‘twofold Heck/6π-electrocyclization’ reactions of di-, tri- and tetrabromoindoles

  2011cites this paper
• 1,7-Palladium migration via C-H activation, followed by intramolecular amination: regioselective synthesis of benzotriazoles.

  2011cites this paper
• Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

  2011cites this paper
• Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: application for the total synthesis of clausine C, clausine R, and clauraila A.

  2011cites this paper
• Pd‐, Ni‐, Fe‐, and Co‐Catalyzed Cross‐Couplings Using Functionalized Zn‐, Mg‐, Fe‐, and In‐Organometallics

  2010cites this paper
• Aryl azides formation under mild conditions: a kinetic study in some ionic liquid solutions.

  2010cites this paper
• Efficient Synthesis of Novel Bis(dipyrromethanes) with Versatile Linkers via Indium(III) Chloride‐Catalyzed Condensation of Pyrrole and Dialdehydes

  2010cites this paper
• An expedient synthesis of ellipticine via Suzuki–Miyaura coupling

  2010cites this paper
• Recent advances in transition metal-catalyzed N-atom transfer reactions of azides.

  2010cites this paper
• Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.

  2009cites this paper
• Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl.

  2009cites this paper
• Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

  2009cites this paper
• A Versatile Synthesis of Annulated Carbazole Analogs Involving a Domino Reaction of Bromomethylindoles with Arenes/Heteroarenes

  2009cites this paper
• Synthesis of carbazoles by intramolecular arylation of diarylamide anions.

  2009cites this paper
• Preparation of polyfunctional indazoles and heteroarylazo compounds using highly functionalized zinc reagents.

  2009cites this paper
• A one pot synthesis of annulated carbazole analogs

  2008cites this paper
• Ionic liquids/[bmim][N3] mixtures: promising media for the synthesis of aryl azides by SNAr.

  2008cites this paper
• Tricyclic Systems: Central Carbocyclic Ring with Fused Five- and Six-membered Rings

  2008cites this paper
• First total synthesis of clausine L and pityriazole, a metabolite of the human pathogenic yeast Malassezia furfur.

  2008cites this paper
• Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides.

  2008cites this paper
• Efficient transformation of azides to primary amines using the mild and easily accessible CeCl3.7H2O/NaI system.

  2008cites this paper
• 1‐Aryl‐3,3‐diisopropyltriazenes: An Easily Accessible and Particularly Stable Class of Triazenes Towards Strong Basic and Lewis Acid Conditions

  2008cites this paper
• Preparation of Polyfunctional Aryl Azides from Aryl Triazenes. A New Synthesis of Ellipticine, 9‐Methoxyellipticine, Isoellipticine, and 7‐Carbethoxyisoellipticine.

  2008cites this paper