About: Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides

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About: Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : wasabi.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides
Creator	Balzarini, Jan De Clercq, Erik Lakshman, Mahesh Lagisetty, Pallavi Thomson, Paul
Source	Medline; PMC
abstract	Palladium-catalyzed C–N bond forming reactions of 6-bromo- as well as 6-chloropurine ribonucleosides and the 2’-deoxy analogues with aryl amines are described. Efficient conversions were observed with Pd(OAc)(2)/Xantphos/Cs(2)CO(3), in PhMe at 100 °C. Reactions of the bromo nucleoside derivatives could be conducted at a lowered catalytic loading (5 mol % Pd(OAc)(2)/7.5 mol % Xantphos), whereas good product yields were obtained with a higher catalyst load (10 mol % Pd(OAc)(2)/15 mol % Xantphos) when the chloro analogue was employed. Among the examples evaluated, silyl protection for the hydroxyls appears better as compared to acetyl. The methodology has been evaluated via reactions with a variety of aryl amines and by synthesis of biologically relevant deoxyadenosine and adenosine dimers. This is the first detailed analysis of aryl amination reactions of 6-chloropurine nucleosides, and comparison of the two halogenated nucleoside substrates.
has issue date	2010-07-02(xsd:dateTime)
bibo:doi	10.1002/adsc.200900728
bibo:pmid	21818182
has license	green-oa
sha1sum (hex)	b8a3f8954b01cbe1a0e3e3bbbb2c79b86f16ea72
schema:url	https://doi.org/10.1002/adsc.200900728
resource representing a document's title	Palladium-Catalyzed Aryl Amination Reactions of 6-Bromo- and 6-Chloropurine Nucleosides
has PubMed Central identifier	PMC3148652
has PubMed identifier	21818182
schema:publication	Advanced Synthesis & Catalysis
resource representing a document's body	covid:b8a3f8954b01cbe1a0e3e3bbbb2c79b86f16ea72#body_text
is schema:about of	named entity 'bond' named entity 'load' named entity 'nucleoside' named entity 'Reactions' named entity 'nucleosides' named entity 'Amination' named entity 'BIOLOGICALLY' named entity 'DETAILED' named entity 'LOAD' covid:arg/b8a3f8954b01cbe1a0e3e3bbbb2c79b86f16ea72 named entity 'aryl' named entity 'The' named entity 'OAc' named entity 'variety' named entity 'This' named entity 'OAc' named entity 'mol%' named entity 'OAc' named entity 'Xantphos' named entity 'Xantphos' named entity 'Xantphos' named entity 'dimers' named entity 'substrates' named entity 'Amination' named entity 'Nucleosides' named entity 'p-toluidine' named entity 'deoxyadenosine' named entity 'Arylation' named entity 'aryl' named entity 'amination' named entity 'PhMe' named entity 'deoxyguanosine' named entity 'antiproliferative' named entity 'molar' named entity 'aryl' named entity 'PPh' named entity 'anomeric carbon' named entity 'nucleoside' named entity 'p-toluidine' named entity 'solvent' named entity 'adenosine' named entity 'amination' named entity 'biomimetic synthesis' named entity 'amination' named entity 'proton' named entity 'amination' named entity 'sugar' named entity 'tert-butyldimethylsilyl' named entity 'substrates' named entity 'amination' named entity 'Ligands' named entity 'acetyl' named entity 'alumina' named entity 'sterically' named entity 'phenyl' named entity 'biological properties' named entity 'purine' named entity 'low yielding' named entity 'nucleosides' named entity 'bromination' named entity 'nucleosides' named entity 'DNA cross-link' named entity 'deoxyadenosine' named entity 'bromo' named entity 'protecting groups' named entity 'physiological' named entity 'amination' named entity 'protonated' named entity 'OAc' named entity 'OAc' named entity 'nucleosides' named entity 'o-anisidine' named entity 'antiviral' named entity 'nucleosides' named entity 'biphenyl' named entity 'substrate' named entity 'PhMe'

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