ISSN:
0075-4617
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Syntheses in the Heterocyclic Series, XVII1). Syntheses and Reactions of Pyrimidine-5-carbaldehydes.Formylation of the 6-oxo-4-hydroxydihydropyrimidines 1 with dimethylformamide chloride to N,N-dimethyl-N-(6-oxo-4-hydroxy-3,6-dihydro-5-pyrimidinyl)methyleneimonium chlorides 2 are described. 2 reacts with water to the 6-oxo-4-hydroxy-3,6-dihydropyrimidine-5-carbaldehydes 3, with phosphorous oxide chloride to the 4,6-dichloropyrimidine-5-carbaldehydes 4, with phenylhydrazine to the 6-oxo-4-hydroxy-5-phenylhydrazonomethylenedihydropyrimidines 5 and with malonic ester to the 5-hydroxy-3-ethoxycarbonylpyrimido[4,5-b]-α-pyrones 7. Catalytic dehalogenation of 4,6-dichlorpyrimidine-5-carbaldehyde (4a) yields pyrimidine-5-carbaldehyde (10), which is able to undergo most of the aldehyde reactions under mild conditions.
Notes:
Es wird die Formylierung der 6-Oxo-4-hydroxy-dihydropyrimidine 1 mit Dimethylformamid-chlorid zu N.N-Dimethyl-N-(6-oxo-4-hydroxy-3.6-dihydro-5-pyrimidinyl)-methyenimonium-chloriden 2 beschrieben, sowie die Umsetzung von 2 mit Wasser zu den 6-Oxo-4-hydroxy-3.6-dihydro-pyrimidin-5-carbaldehyden 3, mit Phosphoroxychlorid zu den 4.6-Dichlor-pyrimidin-5-carbaldehyden 4, mit Phenylhydrazin zu den 6-Oxo-4-hydroxy-5-phenylhydrazonomethylen-dihydropyrimidinen 5 und mit Malonester zu den 5-Hydroxy-3-äthoxycarbonyl-pyrimido[4.5-b]-α-pyronen 7. Die katalytische Dehalogenierung von 4.6-Dichlor-pyrimidin-5-carbaldehyd (4a) führt zum Pyrimidin-5-carbaldehyd (10), der unter milden Bedingungen den meisten Aldehyd-Reaktionen zugänglich ist.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.19727660109
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