Cargando…

A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes

[Image: see text] Indoles are converted into α-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolyl aldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 °C under microwave irradiation undergo loss of the...

Descripción completa

Detalles Bibliográficos
Autores principales:	Markey, Sophie J., Lewis, William, Moody, Christopher J.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2013
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971735/ https://www.ncbi.nlm.nih.gov/pubmed/24280001 http://dx.doi.org/10.1021/ol403191k

Ejemplares similares

Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
por: Aksenov, Nicolai A., et al.
Publicado: (2023)

Cascade aza-Wittig/6π-Electrocyclization in the Synthesis of 1,6-Dihydropyridines
por: Polychronidou, Vasiliki, et al.
Publicado: (2021)

Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines
por: Haut, Franz-Lucas, et al.
Publicado: (2021)

No Acid Required: 4π and 6π Electrocyclization Reactions of Dienyl Diketones for the Synthesis of Cyclopentenones and 2H-Pyrans
por: Jacob, Steven D., et al.
Publicado: (2014)

Efficient synthesis of cyclic amidine-based fluorophores via 6π-electrocyclic ring closure
por: Li, Guofeng, et al.
Publicado: (2020)

Terminal Substituent Effects on the Reactivity, Thermodynamics, and Stereoselectivity of the 8π–6π Electrocyclization Cascades of 1,3,5,7-Tetraenes
por: Patel, Ashay, et al.
Publicado: (2014)

Electrocyclic reactions : from fundamentals to research
por: Ansari, Farzana Latif
Publicado: (1999)

Restriction of the conrotatory motion in photo-induced 6π electrocyclic reaction: formation of the excited state of the closed-ring isomer in the cyclization
por: Nagasaka, Tatsuhiro, et al.
Publicado: (2020)

Synthesis of cis-thiiranes as diastereoselective access to epoxide congeners via 4π-electrocyclization of thiocarbonyl ylides
por: Song, Su-min, et al.
Publicado: (2022)

Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives
por: Sun, Xi-Shang, et al.
Publicado: (2022)

Stereoselective Synthesis of Tropanes via a 6π‐Electrocyclic Ring‐Opening/ Huisgen [3+2]‐Cycloaddition Cascade of Monocyclopropanated Heterocycles
por: Sonnleitner, Carina M., et al.
Publicado: (2020)

Engineering of indole-based tethered biheterocyclic alkaloid meridianin into β-carboline-derived tetracyclic polyheterocycles via amino functionalization/6-endo cationic π-cyclization
por: Agarwal, Piyush Kumar, et al.
Publicado: (2012)

Computational insights into the mechanisms and origins of switchable selectivity in gold(i)-catalyzed annulation of ynamides with isoxazoles via 6π-electrocyclizations of azaheptatrienyl cations
por: Badeji, Abosede Adejoke, et al.
Publicado: (2023)

C7‐Indole Amidations and Alkenylations by Ruthenium(II) Catalysis
por: Choi, Isaac, et al.
Publicado: (2020)

Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations
por: Giri, Sovan Sundar, et al.
Publicado: (2018)

Regio- and Enantioselective (Het)arylation of β-Alkenyl Pyrroline to α-Aryl-β-alkenyl Pyrrolidines
por: Dwari, Soumita, et al.
Publicado: (2019)

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment
por: Milyutin, Constantine V, et al.
Publicado: (2023)

Photoinduced Changes in Aromaticity Facilitate Electrocyclization of Dithienylbenzene Switches
por: Oruganti, Baswanth, et al.
Publicado: (2020)

Rehybridization dynamics into the pericyclic minimum of an electrocyclic reaction imaged in real-time
por: Liu, Y., et al.
Publicado: (2023)

Mechanochemical Synthesis and Isomerization of N-Substituted Indole-3-carboxaldehyde Oximes †
por: Baláž, Matej, et al.
Publicado: (2019)

Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates
por: Lefranc, Julien, et al.
Publicado: (2013)

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst
por: Paul, Abhijit, et al.
Publicado: (2020)

Synthesis of Cyclic Alkenylsiloxanes by Semihydrogenation: A Stereospecific Route to (Z)-Alkenyl Polyenes
por: Elbert, Bryony L, et al.
Publicado: (2014)

Electron‐Rich Diruthenium Complexes with π‐Extended Alkenyl Ligands and Their F(4)TCNQ Charge‐Transfer Salts
por: Das, Rajorshi, et al.
Publicado: (2022)

Decarboxylative Alkenylation
por: Edwards, Jacob T., et al.
Publicado: (2017)

Variations on the Bergman Cyclization Theme: Electrocyclizations of Ionic Penta-, Hepta-, and Octadiynes
por: Sirianni, Dominic A., et al.
Publicado: (2023)

Discovery of Novel α-Carboline Inhibitors of the Anaplastic Lymphoma Kinase
por: Mologni, Luca, et al.
Publicado: (2022)

Condensation Reactions of 3-Oxo-2-arylhydrazonopropanals with Active Methylene Reagents: Formation of 2-Hydroxy- and 2-Amino-6-substituted-5-arylazonicotinates and Pyrido[3,2-c]cinnolines via 6π-Electrocyclization Reactions
por: Al-Mousawi, Saleh M., et al.
Publicado: (2012)

Design and synthesis of thiadiazolo-carboxamide bridged β-carboline-indole hybrids: DNA intercalative topo-IIα inhibition with promising antiproliferative activity
por: Tokala, Ramya, et al.
Publicado: (2020)

Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles
por: Velezheva, V. S., et al.
Publicado: (2019)

Antiviral activities of plant-derived indole and β-carboline alkaloids against human and avian influenza viruses
por: Hegazy, Akram, et al.
Publicado: (2023)

Different N—H⋯π interactions in two indole derivatives
por: Kerr, Jamie R., et al.
Publicado: (2016)

Rhodium(i)-catalyzed C6-selective C–H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids
por: Zhao, Haoqiang, et al.
Publicado: (2019)

On the Mechanism of the Formal [2+2] Cycloaddition – Retro‐electrocyclization (CA‐RE) Reaction
por: Hansen, Jonathan Kirschner Solberg, et al.
Publicado: (2022)

Correction to “Discovery of Novel α-Carboline Inhibitors of the Anaplastic Lymphoma Kinase”
por: Mologni, Luca, et al.
Publicado: (2022)

Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight
por: Zeng, Jie, et al.
Publicado: (2020)

Asymmetric hydroalkylation of alkynes and allenes with imidazolidinone derivatives: α-alkenylation of α-amino acids
por: Panahi, Farhad, et al.
Publicado: (2021)

2,6-Dichlorobenzaldehyde oxime
por: Bao, Feng-Yu
Publicado: (2008)

Copper mediated C–H amination with oximes: en route to primary anilines
por: Xu, Lin-Lin, et al.
Publicado: (2018)

TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis
por: Annes, Sesuraj Babiola, et al.
Publicado: (2018)

Cannot write session to /tmp/vufind_sessions/sess_k7dm1gmgctm0r84p2o394a7aag