Coupling-isomerization-N,S-ketene acetal-addition sequences--a three-component approach to highly fluorescent pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines

The Journal of Organic Chemistry
Oana G SchrammThomas J J Müller

Abstract

Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cyclocondensation sequence of an electron-poor (hetero)aryl halide, a terminal propargyl N-tosylamine, and an N,S-ketene acetal. After the coupling-isomerization sequence, a Diels-Alder reaction with inverse electron demand of the intermediate enimine and the N,S-ketene acetal and subsequent aromatization furnish annelated 2-amino pyridines 4 that were unambiguously characterized by numerous X-ray structure analyses. These heterocycles are highly fluorescent and partially pH sensitive, and their electronic structure was studied with spectroscopic and computational methods.

References

May 1, 1977·Journal of Medicinal Chemistry·J L KelleyE W McLean
Apr 15, 2000·Angewandte Chemie·S ShimizuC Hirai
Oct 20, 2000·Chemistry : a European Journal·H BienaymeP Schmitt
Dec 16, 2004·Angewandte Chemie·Thomas WichardGeorg Pohnert

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Citations

Jun 20, 2007·Chemical Society Reviews·Daniel M D'Souza, Thomas J J Müller
Oct 7, 2006·Chemical Communications : Chem Comm·Daniel M D'SouzaThomas J J Müller
Nov 11, 2008·Chemical Communications : Chem Comm·Bas GroenendaalRomano V A Orru
Jan 14, 2016·Chemical Reviews·Lin ZhangQun Liu
Jan 26, 2008·Organic & Biomolecular Chemistry·Daniel M D'SouzaThomas J J Müller
Jun 26, 2008·Chemistry : a European Journal·Nicolas Isambert, Rodolfo Lavilla
Jun 10, 2011·Chemical Society Reviews·Jean-Christophe M MonbaliuChristian V Stevens
Jul 6, 2010·Organic Letters·Daniel M D'SouzaThomas J J Müller

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