Online citations, reference lists, and bibliographies.
← Back to Search

Regio- And Chemoselective Multiple Functionalization Of Chloropyrazine Derivatives. Application To The Synthesis Of Coelenterazine.

M. Mosrin, T. Bresser, P. Knochel
Published 2009 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
Successive regio- and chemoselective metalations of chloropyrazines using TMPMgCl x LiCl and TMPZnCl x LiCl furnish, after trapping with electrophiles, highly functionalized pyrazines in high yields. Application to a synthesis of coelenterazine, a bioluminescent natural product in jellyfish Aequorea victoria, in nine steps (9% overall yield) is reported.



This paper is referenced by
10.1002/ANGE.201204526
Luftstabile feste aromatische und heterocyclische Zinkreagentien durch hochselektive Metallierungen für Negishi-Kreuzkupplungen†
Christos I. Stathakis (2012)
10.1016/J.TET.2010.12.001
Suzuki–Miyaura coupling for general synthesis of dehydrocoelenterazine applicable for 6-position analogs directing toward bioluminescence studies
Wong Phakhodee (2011)
10.1021/acs.orglett.6b00190
Lewis Acid Triggered Regioselective Magnesiation and Zincation of Uracils, Uridines, and Cytidines.
Lydia Klier (2016)
10.1016/j.ejmech.2010.04.040
Chemistry around imidazopyrazine and ibuprofen: discovery of novel fatty acid amide hydrolase (FAAH) inhibitors.
Frédéric De Wael (2010)
10.1007/978-3-319-38878-6_1
Electrophilic Amination for the Synthesis of Alkyl and Aryl Amines
Stacey L. McDonald (2016)
10.1002/ANGE.201006641
Selektive Magnesierung oder Zinkierung hochfunktionalisierter Alkene und Cycloalkene mit 2,2,6,6-Tetramethylpiperidylbasen†
T. Bresser (2011)
10.1021/acs.chemrev.7b00021
C-H Functionalization of Azines.
Kei Murakami (2017)
10.1021/ol5031266
A one-pot copper catalyzed biomimetic route to N-heterocyclic amides from methyl ketones via oxidative C-C bond cleavage.
P. Subramanian (2014)
10.1002/anie.201311029
Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation.
Stacey L. McDonald (2014)
10.1021/cr3002966
Mixed AggregAte (MAA): a single concept for all dipolar organometallic aggregates. 2. Syntheses and reactivities of homo/heteroMAAs.
F. Mongin (2013)
10.1021/acs.joc.5b00036
Synthesis of pyrazines from rhodium-catalyzed reaction of 2H-Azirines with N-sulfonyl 1,2,3-triazoles.
T. Ryu (2015)
10.1021/ACS.ORGLETT.6B03270
Directed Zincation with TMPZnCl·LiCl and Further Functionalization of the Tropolone Scaffold.
Diana Haas (2016)
10.1016/j.bmc.2014.05.044
Molecular mechanism of Symplectoteuthis bioluminescence--part 4: chromophore exchange and oxidation of the cysteine residue.
Chun-ming Chou (2014)
10.1002/047084289X.RN01806
Lithium Dichloro(2,2,6,6‐tetramethylpiperidinato)‐zincate
Thomas Klatt (2015)
10.1016/J.TETLET.2014.09.065
Efficient synthesis and antioxidant activity of coelenterazine analogues
Yueting Lu (2014)
Directed Magnesiation and Zincation of Highly Substituted Alkenes and N-Heterocycles Using 2,2,6,6-Tetramethylpiperidyl Bases. Application to the Total Synthesis of Coelenterazine
T. Bresser (2011)
10.1002/anie.201006641
Selective magnesiation or zincation of highly functionalized alkenes and cycloalkenes using 2,2,6,6-tetramethylpiperidyl bases.
T. Bresser (2011)
10.1002/0471264180.or100.02
Generation and Trapping of Functionalized Aryl‐ and Heteroarylmagnesium and ‐Zinc Compounds
Ferdinand H Lutter (2019)
10.1016/J.TET.2018.08.040
Xanthate-mediated intermolecular alkylation of pyrazines
Q. Huang (2018)
10.1021/jacs.8b11466
Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
J. Li (2019)
10.1016/J.TET.2018.12.018
Recent applications of magnesium- and Zinc-TMP amides in the synthesis of bioactive targets
R. H. V. Nishimura (2019)
10.1002/anie.201101960
Regio- and chemoselective metalation of arenes and heteroarenes using hindered metal amide bases.
B. Haag (2011)
10.1002/anie.202005372
A Predictive Model Towards Site‐Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl⋅LiCl
Moritz Balkenhohl (2020)
10.1021/ic200562h
Structurally powered synergic 2,2,6,6-tetramethylpiperidine bimetallics: new reflections through lithium-mediated ortho aluminations.
R. Mulvey (2011)
10.1002/CHIN.200948170
Regio- and Chemoselective Multiple Functionalization of Chloropyrazine Derivatives. Application to the Synthesis of Coelenterazine.
Marc Mosrin (2009)
10.1021/jo500297r
Strategies to prepare and use functionalized organometallic reagents.
Thomas Klatt (2014)
10.1016/J.JORGANCHEM.2017.07.012
A heterogeneous gold(I)-catalyzed cascade annulation of aldehydes with propargylamine leading to 3-substituted 2,5-dimethylpyrazines
Q. Nie (2017)
10.1002/ANGE.201403688
In‐situ‐Abfangmethode zur Metallierung funktionalisierter Arene und Heteroarene mit TMPLi in Gegenwart von ZnCl2 und anderen Metallsalzen
Annette Frischmuth (2014)
10.1002/anie.201403688
New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts.
Annette Frischmuth (2014)
10.1002/chem.201201485
Preparations and reactions of SF5-substituted aryl and heteroaryl derivatives via Mg and Zn organometallics.
Annette Frischmuth (2012)
10.1002/9783527335855.MARPROD202
Cnidaria and Ctenophora–2
Jean-Michel Kornprobst (2014)
10.1021/ACSCATAL.5B02718
Recent Developments in Negishi Cross-Coupling Reactions
Diana Haas (2016)
See more
Semantic Scholar Logo Some data provided by SemanticScholar