Article

A New Class of Pyrazolopyridine Nucleus with Fluorescent Properties, Obtained through Either a Radical or a Pd Arylation Pathway from N-Azinylpyridinium N-Aminides

Departamentos de Química Orgánica and Química Física, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain
J. Org. Chem., 2008, 73 (22), pp 8800–8807
DOI: 10.1021/jo801549u
Publication Date (Web): October 20, 2008
Copyright © 2008 American Chemical Society
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Departamento de Química Orgánica.

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Departamento de Química Física.

Abstract

Abstract Image

The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives—both of which incorporate a 3-aryl moiety—can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported.

Supporting Information


Experimental procedures and copies of 1H and 13C spectra for selected compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 1,559 Times
Received 17 July 2008
Published online 20 October 2008
Published in print 21 November 2008
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