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Synlett 2012; 23(15): 2227-2230
DOI: 10.1055/s-0032-1317032
letter
© Georg Thieme Verlag Stuttgart · New York

Furo[3,4-b]chromones, and not Pyrano[3,4-b]chromones, are Obtained by the Reaction of 3-Formylchromones with Isocyanides

Ana G. Neo
a   Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain, Fax: +34(927)257110   eMail: cfernan@unex.es
,
Leda Garrido
a   Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain, Fax: +34(927)257110   eMail: cfernan@unex.es
,
Jesús Díaz
a   Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain, Fax: +34(927)257110   eMail: cfernan@unex.es
,
Stefano Marcaccini
b   Dipartimento di Chimica ‘Ugo Schiff’, Università di Firenze, 50019 Sesto Fiorentino FI, Italy
,
Carlos F. Marcos*
a   Laboratorio de Química Orgánica y Bioorgánica (L.O.B.O.), Departamento de Química Orgánica e Inorgánica, Facultad de Veterinaria, Universidad de Extremadura, 10071 Cáceres, Spain, Fax: +34(927)257110   eMail: cfernan@unex.es
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Publikationsverlauf

Received: 14. Juni 2012

Accepted after revision: 13. Juli 2012

Publikationsdatum:
24. August 2012 (online)

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Abstract

The reaction of formylchromones with alkyl isocyanides was reinvestigated. In earlier reports from other research groups, two different structures were proposed for the products of this reaction. Herein, we provide unambiguous evidence that these products are chromenylmethylene furochromenones and not pyrano­chromones. Our structure assignment is based on X-ray diffraction analysis and two-dimensional NMR methods. The knowledge of the correct structure of these compounds is essential for the design of derivatives with potential applications as bioactive molecules or fluorescent biomarkers.

Key words

cycloaddition reactions - furans - fused-ring systems - multicomponent reactions - heterocycles - natural products

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information

Primary Data

    for this article are available online at ­http://www.thieme-connect.com/ejournals/toc/synlett and can be cited using the following DOI:
  • Primary Data
 

  • References and Notes

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