Synthesis
DOI: 10.1055/a-2685-9214
Paper

Phospha-Michael reaction on 4H-Chromen-4-one: A Useful Application for the Synthesis of Phosphorated 4-Oxochromanes, 4-Hydroxychromanes and 4-Oxo-4H-chromenes

1   Centro de Investigaciones Quimicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Mexico
2   CENTRO DE INVESTIGACIONES QUIMICAS, UNIVERSIDAD AUTONOMA DEL ESTADO DE MORELOS, CUERNAVACA, Mexico
,
Saúl Esteban Eloisa-Pizaña
3   Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos Centro de Investigaciones en Ciencias, Cuernavaca, Mexico (Ringgold ID: RIN528999)
,
4   Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos Centro de Investigaciones Químicas, Cuernavaca, Mexico (Ringgold ID: RIN428215)
,
Rubén Oswaldo Argüello-Velasco
5   Facultad de Ciencias Químicas e Ingeniería, Universidad Autónoma del Estado de Morelos Facultad de Ciencias Químicas e Ingeniería, Cuernavaca, Mexico (Ringgold ID: RIN528983)
› Author Affiliations

Supported by: Secretaría de Ciencia, Humanidades, Tecnología e Innovación (SECIHTI) 140607,286614
Preview

We report here a practical method for the synthesis of dimethyl (4-oxochroman-2-yl)phosphonate and ethyl (4-oxochroman-2-yl)phenyl-phosphinate through regioselective phospha-Michael addition on chromone followed by the first high diastereoselective reduction with NaBH4 to obtain the novel dimethyl cis-(4-hidroxychroman-2-yl)phosphonate and ethyl cis-(4-hidroxychroman-2-yl)phenylphosphinate, which using the Mitsunobu reaction were converted into trans diastereoisomers. Additionally, dimethyl (4-oxo-chroman-2-yl)phosphonate and ethyl (4-oxochroman-2-yl)phenylphosphinate were transformed into (4-oxo-4H-chromen-2-yl)phosphonic acid and (4-oxo-4H-chromen-2-yl)phenylphosphinic acid, analogues of 4-oxo-4H-chromene-2-carboxylic acid.



Publication History

Received: 03 July 2025

Accepted after revision: 18 August 2025

Accepted Manuscript online:
18 August 2025

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