Phosphonylation of 3-Substituted 2H-Benzo[b][1,4]oxazin-2-ones and Quinoxalin-2(1H)‑ones with Dialkylphosphites Under mild Conditions: Access to Diverse Heterocyclic α-Aminophosphonates

An efficient protocol for the phosphonylation of 3-substituted quinoxalin-2(1H)‑ones and 2H-benzo[b][1,4]oxazin-2-ones with dialkylphosphites has been developed. This method provides a novel and more sustainable approach to access structurally diverse quaternary heterocyclic α-aminophosphonates in good yields under solvent and metal-free conditions. Additionally, we report the phosphonylation of 3,4-dihydroquinoxalin-2(1H)-one via the corresponding N-acyl iminium ion, providing efficient access to (1,2,3,4-tetrahydroquinoxalin-2-yl)phosphonate in good yield.

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Publication Details

Journal
Synthesis
Published
2026-03-27
DOI
https://doi.org/10.1055/a-2844-1923
Primary Topic
Organophosphorus compounds synthesis
Type
article
Field-Weighted Citation Impact
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article

Phosphonylation of 3-Substituted 2H-Benzo[b][1,4]oxazin-2-ones and Quinoxalin-2(1H)‑ones with Dialkylphosphites Under mild Conditions: Access to Diverse Heterocyclic α-Aminophosphonates

Mario Ordóñez, Itzel Bernal-Evangelista, Ivan Romero-Estudillo, Rubén Oswaldo Argüello-Velasco
Synthesis
Organophosphorus compounds synthesis
article

Phosphonylation of 3-Substituted 2H-Benzo[b][1,4]oxazin-2-ones and Quinoxalin-2(1H)‑ones with Dialkylphosphites Under mild Conditions: Access to Diverse Heterocyclic α-Aminophosphonates

Mario Ordóñez, Itzel Bernal-Evangelista, Ivan Romero-Estudillo, Rubén Oswaldo Argüello-Velasco
article en

Abstract

An efficient protocol for the phosphonylation of 3-substituted quinoxalin-2(1H)‑ones and 2H-benzo[b][1,4]oxazin-2-ones with dialkylphosphites has been developed. This method provides a novel and more sustainable approach to access structurally diverse quaternary heterocyclic α-aminophosphonates in good yields under solvent and metal-free conditions. Additionally, we report the phosphonylation of 3,4-dihydroquinoxalin-2(1H)-one via the corresponding N-acyl iminium ion, providing efficient access to (1,2,3,4-tetrahydroquinoxalin-2-yl)phosphonate in good yield.

Synthesis
Universidad Autónoma del Estado de Morelos (MX)
Responsible consumption and production
Openalex Percentile: Top 6%
Organophosphorus compounds synthesis
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