Synthesis of a Naphtho-pyrido-Annulated Iodonium Salt and Pd-Catalyzed Transformation to 7H-Naphtho[1,8-bc][1,5]naphthyridine

Julien Letessier; Mario Geffe; Dieter Schollmeyer; Heiner Detert

doi:10.1055/s-0033-1338530

Synthesis, Table of Contents

Synthesis 2013; 45(22): 3173-3178
DOI: 10.1055/s-0033-1338530

paper

Synthesis of a Naphtho-pyrido-Annulated Iodonium Salt and Pd-Catalyzed Transformation to 7H-Naphtho[1,8-bc][1,5]naphthyridine

Authors

Julien Letessier

Institute for Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10–14, 55099 Mainz, Germany Fax: +49(6131)3925338 Email: detert@uni-mainz.de
Mario Geffe

Institute for Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10–14, 55099 Mainz, Germany Fax: +49(6131)3925338 Email: detert@uni-mainz.de
Dieter Schollmeyer

Institute for Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10–14, 55099 Mainz, Germany Fax: +49(6131)3925338 Email: detert@uni-mainz.de
Heiner Detert*

Institute for Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10–14, 55099 Mainz, Germany Fax: +49(6131)3925338 Email: detert@uni-mainz.de

Abstract

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Dedicated to Heinz Kolshorn on the occasion of his 70^th birthday

Abstract

Nitropyridylnaphthalene is the central intermediate for the synthesis of naphthonaphthyridine and benzo-δ-carboline. Whereas the Cadogan reaction gives the carboline, transformation of the nitro group to iodo followed by oxidation and cyclization results in an iodonium salt. A twofold Pd-catalyzed amination leads to the naphthyridine.

Key words

amination - fused-ring systems - heterocycles - iodine - palladium - catalysis

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References

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Supplementary Material

Supporting Information (PDF)