Issue 22, 2022
From the journal:

Organic & Biomolecular Chemistry

Persulfate-nitrogen doped graphene mixture as an oxidant for the synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters and nitrite†

Palani Natarajan, ORCID logo *a   Priyaa  and  Deachen Chuskita  

* Corresponding authors

a Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh - 160 014, India
E-mail: pnataraj@pu.ac.in

Abstract

A series of 3-nitro-4-aryl-2H-chromen-2-ones in good yields have directly been obtained from aryl alkynoate esters and nitrite by employing a mixture of K2S2O8-nitrogen doped graphene as an oxidant in a watery medium at room temperature. A plausible mechanism for the reaction is also reported. It reveals that the product is formed through a cascade of nitro radical addition, spirocyclization, and ester migration. When compared to known methods for the synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters, this protocol is environmentally friendly, sustainable, practical and energy efficient and does not use a harmful nitro source. Furthermore, nitrogen doped graphene used in this approach can be easily recovered and reused at least four times without losing its activity.

Graphical abstract: Persulfate-nitrogen doped graphene mixture as an oxidant for the synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters and nitrite

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Article information

DOI
https://doi.org/10.1039/D2OB00827K
Article type
Paper
Submitted
01 May 2022
Accepted
16 May 2022
First published
16 May 2022

Org. Biomol. Chem., 2022,20, 4616-4624

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Persulfate-nitrogen doped graphene mixture as an oxidant for the synthesis of 3-nitro-4-aryl-2H-chromen-2-ones from aryl alkynoate esters and nitrite

P. Natarajan, Priya and D. Chuskit, Org. Biomol. Chem., 2022, 20, 4616 DOI: 10.1039/D2OB00827K

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