Events The 19th International Electronic Conference on Synthetic Organic Chemistry

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Published

This submission belongs to the session a. General Organic Synthesis of the event The 19th International Electronic Conference on Synthetic Organic Chemistry

Published date

30 Oct, 2015

Citation

Anastasia Fesenko, Anatoly Shutalev, A Novel Access to Pyrido[4,3-d]pyrimidine Scaffold, in Proceedings of The 19th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2015, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-19-a029

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A Novel Access to Pyrido[4,3-d]pyrimidine Scaffold

Anastasia Fesenko ¹

Anatoly Shutalev ¹

1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation

Abstract

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 1,3-diketone enolates and dehydration of the resulting products under acidic conditions.

Keywords

Pyrido[4,3-d]pyrimidines

Azidoaldehydes

Tetrahydropyrimidines

Amidoalkylation

Staudinger Reaction

aza-Wittig Reaction

Manuscript

Manuscript (sciforum-006498).pdf

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