Pyridinium N-heteroarylaminides: synthesis of N-heteroaryltetramines based on 1,6-bis(phenoxy)hexane and 1,3-bis(phenoxymethyl)benzene

doi:10.1016/j.tetlet.2007.06.044

Tetrahedron Letters

Volume 48, Issue 33, 13 August 2007, Pages 5899-5903

https://doi.org/10.1016/j.tetlet.2007.06.044 Get rights and content

Abstract

The synthesis of a set of new N-heteroaryltetramines is reported. A regioselective alkylation on the N-exo nitrogen of pyridinium N-(heteroaryl)aminide with the corresponding tetrabromo compounds, followed by a clean N–N bond reduction of the corresponding tetra-salts, allowed an easy and general method to obtain N,N′,N″,N‴-tetrakis(2-heteroaryl)tetramines.

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Acknowledgments

The authors thank the Comisión Interministerial de Ciencia y Tecnología (CTQ2005-08902) for financial support, and the Ministerio de Educación y Ciencia (MEC) for a studentship (R.C.).

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Pyridinium N-heteroarylaminides: synthesis of N-heteroaryltetramines based on 1,6-bis(phenoxy)hexane and 1,3-bis(phenoxymethyl)benzene

Abstract

Graphical abstract

Section snippets

Acknowledgments

Acc. Chem. Res.

Synthesis

Chem. Commun.

J. Org. Chem.

Tetrahedron

Angew. Chem., Int. Ed.

Tetrahedron

J. Org. Chem.

J. Am. Chem. Soc.

J. Org. Chem.

J. Am. Chem. Soc.

Tetrahedron Lett.

Tetrahedron Lett.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

Tetrahedron Lett.

Tetrahedron

J. Org. Chem.

Tetrahedron

Tetrahedron

Tetrahedron

Tetrahedron Lett.

Tetrahedron Lett.

Polyamines in Biology and Medicine

Acc. Chem. Res.