A NEW APPROACH TO THE PYRROLO[3,4-<i>d</i>]PYRIMIDINE SYSTEM <i>VIA</i> TANDEM STAUDINGER/AZA-WITTIG REACTION OF 5-ACYL-4-AZIDOMETHYL-3,4-DIHYDROPYRIMIDIN-2(1<i>H</i>)-ONES

Authors

  • Anastasia A. Fesenko N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Mikhail S. Grigoriev Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31, Build. 4 Leninsky Ave., Moscow 119071
  • Anatoly D. Shutalev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

Keywords:

N-[(2-azido-1-tosyl)alkyl]ureas, ureidoalkylation, Staudinger reaction, aza-Wittig reaction., 3,4-dihydropyrimidin-2(1H)-ones, pyrrolo[3,4-d]pyrimidines

Abstract

A novel access to pyrrolo[3,4-d]pyrimidine scaffold via tandem Staudinger/intramolecular aza-Wittig reaction of 5-acyl-4-(1-azidoalkyl)-3,4-dihydropyrimidin-2(1H)-ones promoted by PPh3 was developed. Synthesis of the starting pyrimidinones involved the reaction ofreadily available N-[(2-azido-1-tosyl)alkyl]ureas with Na enolates of benzoylacetone or acetylacetone followed by acid-catalyzed dehydration of the resulting products without their isolation.

Author Biography

Mikhail S. Grigoriev, Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31, Build. 4 Leninsky Ave., Moscow 119071

Кафедра органической химии, заведующий

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Published

2024-01-10

Issue

Vol. 59 No. 11/12 (2023)

Section

Original Papers