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

作者：Fesenko Anastasia A; Shutalev Anatoly D^*

来源：Tetrahedron, 2014, 70(35): 5398-5414.

DOI：10.1016/j.tet.2014.06.128

• Azidoaldehydes
• Tetrahydropyrimidines
• Pyrido[4,3-d]pyrimidines
• Ureidoalkylation
• Staudinger reaction
• Aza-Wittig reaction

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-(beta-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 alpha,beta-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.

• 出版日期2014-9-2