Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones

Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones

6-Substituted 1,3-dimethyl-7-hydroxylumazines (5-7) have been synthesized from 1,3-dimethyluracil-5,6- diamine (1) and a-ketoacid esters (2-4) under weakly acidic conditions. The isomeric 7-substituted 1,3-dimethyllumazin- 6-ones (18-20) resulted from a regioselective Boon synthesis starting from 6-...

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Main Authors: Arendt Reinhardt, Pfleiderer Wolfgang
Format: Article
Language:English
Published: De Gruyter 2005-11-01
Series:Pteridines
Subjects:
lumazines
boon synthesis
lumazine-n-oxides
condensation reactions
Online Access:https://doi.org/10.1515/pteridines.2005.16.4.184
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spelling doaj-06c85a820ba14d02a2edf214390d7e752021-09-05T14:00:02ZengDe GruyterPteridines0933-48072195-47202005-11-0116418418910.1515/pteridines.2005.16.4.184Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-onesArendt Reinhardt0Pfleiderer Wolfgang1Fachbereich Chemie, Universität Konstanz, Postfach 5560, D-78457 Konstanz, GermanyFachbereich Chemie, Universität Konstanz, Postfach 5560, D-78457 Konstanz, Germany6-Substituted 1,3-dimethyl-7-hydroxylumazines (5-7) have been synthesized from 1,3-dimethyluracil-5,6- diamine (1) and a-ketoacid esters (2-4) under weakly acidic conditions. The isomeric 7-substituted 1,3-dimethyllumazin- 6-ones (18-20) resulted from a regioselective Boon synthesis starting from 6-chloro-l,3-dimethyl-5- nitrouracil (8) and α-aminoacid esters (9-11) in a three-step procedure. H202 oxidations led with 6 and 7 to the corresponding 5-N-oxides (21, 22) whereas in the lumazin-6-onc scries only the 7-phenyl derivative (20) reacted also at N-5 position forming a cyclic hydroxamic acid (23). The newly synthesized compounds have been characterized by elemental analyses,1H-NMR and UV spectra based upon pKa-determinations.https://doi.org/10.1515/pteridines.2005.16.4.184lumazinesboon synthesislumazine-n-oxidescondensation reactions
collection DOAJ
language English
format Article
sources DOAJ
author Arendt Reinhardt
Pfleiderer Wolfgang
spellingShingle Arendt Reinhardt
Pfleiderer Wolfgang
Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones
Pteridines
lumazines
boon synthesis
lumazine-n-oxides
condensation reactions
author_facet Arendt Reinhardt
Pfleiderer Wolfgang
author_sort Arendt Reinhardt
title Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones
title_short Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones
title_full Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones
title_fullStr Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones
title_full_unstemmed Pteridines, CXVI. (1) Synthesis and Reactivity of 6-Substituted l,3-Dimethyl-7-hydroxylumazines and 7-Substituted l,3-Dimethyl-(5H)-lumazin-6-ones
title_sort pteridines, cxvi. (1) synthesis and reactivity of 6-substituted l,3-dimethyl-7-hydroxylumazines and 7-substituted l,3-dimethyl-(5h)-lumazin-6-ones
publisher De Gruyter
series Pteridines
issn 0933-4807
2195-4720
publishDate 2005-11-01
description 6-Substituted 1,3-dimethyl-7-hydroxylumazines (5-7) have been synthesized from 1,3-dimethyluracil-5,6- diamine (1) and a-ketoacid esters (2-4) under weakly acidic conditions. The isomeric 7-substituted 1,3-dimethyllumazin- 6-ones (18-20) resulted from a regioselective Boon synthesis starting from 6-chloro-l,3-dimethyl-5- nitrouracil (8) and α-aminoacid esters (9-11) in a three-step procedure. H202 oxidations led with 6 and 7 to the corresponding 5-N-oxides (21, 22) whereas in the lumazin-6-onc scries only the 7-phenyl derivative (20) reacted also at N-5 position forming a cyclic hydroxamic acid (23). The newly synthesized compounds have been characterized by elemental analyses,1H-NMR and UV spectra based upon pKa-determinations.
topic lumazines
boon synthesis
lumazine-n-oxides
condensation reactions
url https://doi.org/10.1515/pteridines.2005.16.4.184
work_keys_str_mv AT arendtreinhardt pteridinescxvi1synthesisandreactivityof6substitutedl3dimethyl7hydroxylumazinesand7substitutedl3dimethyl5hlumazin6ones
AT pfleidererwolfgang pteridinescxvi1synthesisandreactivityof6substitutedl3dimethyl7hydroxylumazinesand7substitutedl3dimethyl5hlumazin6ones
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