Affiliation:
1. Pharmazeutisches Institut, Abteilung für Pharmazeutische Chemie, Christian-Albrechts-Universität Kiel, Gutenbergstraße 76, D-24118 Kiel
Abstract
The Mannich reaction of 7-aryl-5,6-dihydropyrido[2,3-d]pyrimidines 3, easily accessible by condensation of 6-amino-1,3-dimethyluracil (1) with Mannich bases 2a - c, gives rise to a mixture of 7-aryl-6-(N,N-dimethylaminomethyl)pyrido[2,3-d]pyrimidines 6 and 7 as well as 1,2-bis- (7-arylpyrido[2,3-d]pyrimidin-6-yl)ethane 13 the ratio of which depends on the reaction conditions and the amine used. 6-Alkylamino-1,3-dimethyluracils 15 - 18 were converted to the corresponding 5-(3-oxo-3-phenylpropyl)uracils 19 - 22 by condensation with the Mannich base 2a. Ring closure of 19 - 22 was performed by Vilsmeier formylation to afford the 8-alkyl- and 7,8-diaryl-5,8- dihydropyrido[2,3-d]pyrimidine-6-carbaldehydes 9 - 12 via the corresponding iminium salts 27 - 30
Cited by
5 articles.
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1. Review of the Synthesis, Reactions and Pharmaceutical Potential of Pyrido
[2,3-d]Pyrimidine Derivatives;Current Organic Chemistry;2023-02
2. Efficient Synthesis of Uracil-Derived Hexa- and Tetrahydropyrido[2,3-d]pyrimidines;European Journal of Organic Chemistry;2013-07-04
3. Vilsmeier Formylation;Comprehensive Organic Name Reactions and Reagents;2010-09-15
4. Unexpected Sodium Methoxide-catalyzed Rearrangement of 6-Amino-5-aroyl-1,3-dimethyluracils to Form Novel Cinnamoamides;Zeitschrift für Naturforschung B;2009-06-01
5. Two-Step Synthetic Approach to 6-Substituted Pyrido[2,3-d]pyrimidine(1H,3H)-2,4-diones from 6-Amino-, 6-Alkylamino-, and 6-Arylamino-1,3-dimethyluracils.;ChemInform;2006-09-12