Issue 17, 2012
From the journal:

Organic & Biomolecular Chemistry

Conjugate addition of isocyanides to chromone 3-carboxylic acid: an efficient one-pot synthesis of chroman-4-one 2-carboxamides†

Ana G. Neo,a   Jesús Díaz,a   Stefano Marcaccinib  and  Carlos F. Marcos*a  

* Corresponding authors

a Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Dept Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain
E-mail: cfernan@unex.es

b HeteroBioLab, Dipartimento di Chimica Organica, Università di Firenze, 50019 Sesto, Fiorentino (FI), Italy

Abstract

We report a novel Lewis acid catalysed tandem reaction of isocyanides, chromone 3-carboxylic acid and nucleophiles. An experimentally very simple procedure, involving the use of microwave irradiation in the presence of a Lewis acid catalyst, affords a representative collection of chromone-2-carboxamides and chromone-2-carboxamido-3-esters in high yields, in just a few minutes. Such an unprecedented strategy is formally equivalent to a conjugate addition of isocyanides to Michael acceptors.

Graphical abstract: Conjugate addition of isocyanides to chromone 3-carboxylic acid: an efficient one-pot synthesis of chroman-4-one 2-carboxamides

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Article information

DOI
https://doi.org/10.1039/C2OB07011A
Article type
Paper
Submitted
30 Nov 2011
Accepted
13 Feb 2012
First published
15 Feb 2012

Org. Biomol. Chem., 2012,10, 3406-3416

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Conjugate addition of isocyanides to chromone 3-carboxylic acid: an efficient one-pot synthesis of chroman-4-one 2-carboxamides

A. G. Neo, J. Díaz, S. Marcaccini and C. F. Marcos, Org. Biomol. Chem., 2012, 10, 3406 DOI: 10.1039/C2OB07011A

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