A novel access to pyrido[4,3-d]pyrimidine scaffold via Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(β-azidoalkyl)-1,2,3,4-tetrahydropyrimidin-2-ones

A general four-step approach to 1,2,3,7,8,8a-hexahydropyrido[4,3-d]pyrimidin-2-ones via Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(β-azidoalkyl)-1,2,3,4-tetrahydropyrimidin-2-ones promoted by PPh3 was developed. Synthesis of the starting pyrimidinones included preparation of 3-azidoa...

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Bibliographic Details
Published in:Tetrahedron 2014-09, Vol.70 (35), p.5398-5414
Main Authors: Fesenko, Anastasia A., Shutalev, Anatoly D.
Format: Article
Language:English
Subjects:
Acetylacetone
Aldehydes
Aza-Wittig reaction
Azidoaldehydes
Dehydration
Hydrazoic acid
Pyrido[4,3-d]pyrimidines
Scaffolds
Staudinger reaction
Synthesis
Tetrahedrons
Tetrahydropyrimidines
Transformations
Ureidoalkylation
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Summary:A general four-step approach to 1,2,3,7,8,8a-hexahydropyrido[4,3-d]pyrimidin-2-ones via Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(β-azidoalkyl)-1,2,3,4-tetrahydropyrimidin-2-ones promoted by PPh3 was developed. Synthesis of the starting pyrimidinones included preparation of 3-azidoaldehydes by the addition of hydrazoic acid to α,β-unsaturated aldehydes, transformation of 3-azidoaldehydes into N-[(3-azido-1-tosyl)alkyl]ureas followed by the reaction with enolates of dibenzoylmethane, benzoylacetone, acetylacetone, or ethyl 2,4-dioxo-4-phenylbutanoate and dehydration of the resulting products under acidic conditions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.06.128