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Synthesis 2024; 56(23): 3615-3620
DOI: 10.1055/a-2412-9635
paper

A New General, Mild Preparation of 2-Hydroxy-β-nitrostyrenes Starting from 2-Acetylsalicylaldehydes and Nitroalkanes via Domino Process

Benedetta Bassetti
,
Lu Wang
,
Roberto Ballini
,
Marino Petrini 
,
Alessandro Palmieri  ∗
This study received funding from the European Union - Next-GenerationEU - National Recovery and Resilience Plan (NRRP) – MISSION 4 COMPONENT 2, INVESTMENT N. 1.1, CALL PRIN 2022 PNRR D.D. 1409 del 14-09-22 - Xylonite: the new season of Xylochemistry - Project no. P2022HSF3R – PRIN 2022 PNRR - CUP J53D23014790001.
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Abstract

A new practical and improved preparation of 2-hydroxy-β-nitrostyrenes by reaction of nitroalkanes with acetylsalicylaldehydes, promoted by DBU in acetonitrile at 0 °C is reported. Under these conditions products were isolated in very good yields and as single E-diastereomers.

Key words

nitroalkenes - Henry reaction - domino reaction - nitroaldol condensation - β-nitrostyrenes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2412-9635.
  • Supporting Information


Publication History

Received: 11 August 2024

Accepted after revision: 10 September 2024

Accepted Manuscript online:
10 September 2024

Article published online:
01 October 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
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