Preparation and Synthetic Application of Highly Reactive 6-Trifluoromethanesulfonyloxylllmazine; A Novel Method for 6-Substituted Lumazines

Murata, Shizuaki; Sugimoto, Takashi; Murakami, Katsuhiko

doi:10.1515/pteridines.1997.8.1.1

Cited by 5 publications

(2 citation statements)

References 6 publications

(9 reference statements)

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“…However with highly reactive leaving groups such as triflate, it has been possible to substitute carbanions directly. As noted earlier, triflates can be prepared from the corresponding 5‐ N ‐oxides using triflic anhydride (8) (Scheme ); this reaction parallels the preparation of 6‐halolumazines from the 5‐ N ‐oxide using acetyl chloride or acetyl bromide, the bromolumazine in particular being a useful intermediate for developing diversity‐related reactions in the pteridine field (29). Although the triflates were readily displaced by typical heteroatom nucleophiles, the reactions of most interest were those involving carbon nucleophiles such as 1,3‐diketones and umpolung reagents.…”

Section: Diversity Through Nucleophilic Substitution At the Pteridinementioning

confidence: 98%

The diversity‐oriented synthesis of pteridines—achievements and potential for development

Suckling¹

2013

IUBMB Life

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The importance of pteridines in the key cofactors, tetrahydrofolate and tetrahydrobiopterin, has encouraged the development of the chemistry and chemical biology of pteridines. In order to investigate the latter, versatile synthetic methods are required to prepare designed relatives of the natural cofactors for use as potential drugs or biological probes. Recently, diversity-oriented synthesis has become a particularly powerful and versatile approach to the synthesis of pteridines and related heterocyclic compounds. This article describes and discusses available methods using radical, electrophilic, nucleophilic, and organometal mediated substitution reactions.

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Section: Diversity Through Nucleophilic Substitution At the Pteridinementioning

confidence: 98%

The diversity‐oriented synthesis of pteridines—achievements and potential for development

Suckling¹

2013

IUBMB Life

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“…By similar work-up and purificatio n treatments as the general procedure 6 -phenyl-l ,3 -dimethyllumazine 5-oxide (Sa ) (0 .24 g, 14%) was o btained as pale yello w needles: mp 216-217°C (lit. 13,14 …”

Section: -(4-methylphenyl)-13-dimethyllumazine (2b) and 6-(4-methylmentioning

confidence: 99%

Regioselective Arylation of 1,3-Dimethyllumazine and Its 5-Oxide by Diazonium Salts

Sugimoto¹,

Seo

Murata

et al. 1997

Pteridines

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SummaryA new method to introduce an aryl group directly into the pteridine nucleus by the action of arene diazonium salt in an aqueous alkaline solutio n is described. 1,3-Dimethyllumazine and benzene diazonium chloride reacts in an aqueous solution at pH 8-9 to give 7 -phenyl-1 ,3-dimethyllumazine together with a little of 6-phenyi-1 ,3-dimethyllumazine . The analogous reactions of 1,3-dimethyllumazine with 4-methyl-, 4-methm.),-, 4-chloro-, and 3-chlorobenzene diazonium chlorides give the corresponding 7-aryl-1,3-dimethyllumazines as major products together with a little of 6-aryl-1,3-dimethyllumazines. Reactions of 1,3-dimethyllumazine 5-oxide with arene diazonium salts under the same conditions exclusively afford the corresponding 6-aryl-1,3-dimethyllumazine 5-oxides which are easily converted to 6-aryl-1,3-dimethyllumazine by the action of tributylphosphine. Mechanisms concerning regioselectivities are investigated by using molecular orbital calculations.

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A Selective Procedure for 6-Subsituted Pterin Derivatives: Synthesis and Substitution of Pterin 6-Triflate

Murata

Kujime

Kudoh

2002

Chemistry and Biology of Pteridines and Folates

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Preparation and Synthetic Application of Highly Reactive 6-Trifluoromethanesulfonyloxylllmazine; A Novel Method for 6-Substituted Lumazines

Cited by 5 publications

References 6 publications

The diversity‐oriented synthesis of pteridines—achievements and potential for development

The diversity‐oriented synthesis of pteridines—achievements and potential for development

Regioselective Arylation of 1,3-Dimethyllumazine and Its 5-Oxide by Diazonium Salts

A Selective Procedure for 6-Subsituted Pterin Derivatives: Synthesis and Substitution of Pterin 6-Triflate

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