Preparation of 2,7-Diamino-1,8-naphthyridine: A Useful Building Block for Supramolecular Chemistry

Abstract

A two-step conversion of 2-chloro-7-amido-1,8-naphthyridine to 2,7-diamino-1,8-naphthyridine is described. The process, which involves a nucleophilic aromatic substitution reaction with 4-methoxybenzylamine and subsequent deprotection, can be carried out on a large scale.

heterocycles - nucleophilic aromatic substitution - supramolecular systems - hydrogen bond - amine protecting group

References

<A NAME="RS02405ST-1A">1a</A> Corbin PS. Zimmerman SC. J. Am. Chem. Soc.  1998,  120:  9710 

<A NAME="RS02405ST-1B">1b</A> Corbin PS. Zimmerman SC. J. Am. Chem. Soc.  2000,  122:  3779 

<A NAME="RS02405ST-1C">1c</A> Zimmerman SC. Corbin PS. Struct. Bonding  2000,  96:  63 

<A NAME="RS02405ST-1D">1d</A> Corbin PS. Zimmerman SC. Thiessen PA. Hawryluk NA. Murray TJ. J. Am. Chem. Soc.  2001,  123:  10475 

<A NAME="RS02405ST-1E">1e</A> Corbin PS. Lawless LJ. Li Z.-T. Ma Y. Witmer MJ. Zimmerman SC. Proc. Natl. Acad. Sci. U.S.A.  2002,  99:  5099 

<A NAME="RS02405ST-2A">2a</A> Lüning U. Kühl C. Tetrahedron Lett.  1998,  39:  5735 

<A NAME="RS02405ST-2B">2b</A> Brammer S. Lüning U. Kühl C. Eur. J. Org. Chem.  2002,  4054 

<A NAME="RS02405ST-2C">2c</A> Lüning U. Kühl C. Uphoff A. Eur. J. Org. Chem.  2002,  4063 

<A NAME="RS02405ST-3A">3a</A> Wang X.-Z. Li X.-Q. Shao X.-B. Zhao X. Deng P. Jiang X.-K. Li Z.-T. Chen Y.-Q. Chem. Eur. J.  2003,  9:  2904 

<A NAME="RS02405ST-3B">3b</A> Zhao X. Wang X.-Z. Jiang X.-K. Chen Y.-Q. Li Z.-T. Chen G.-J. J. Am. Chem. Soc.  2003,  125:  15128 

<A NAME="RS02405ST-3C">3c</A> Li X.-Q. Jiang X.-K. Wang X.-Z. Li Z.-T. Tetrahedron  2004,  60:  2063 

<A NAME="RS02405ST-3D">3d</A> Li X.-Q. Feng D.-J. Jiang X.-K. Li Z.-T. Tetrahedron  2004,  60:  8275 

<A NAME="RS02405ST-4">4</A> Ligthart GBWL. Ohkawa H. Sijbesma RP. Meijer EW. J. Am. Chem. Soc.  2005,  127:  810 

<A NAME="RS02405ST-5A">5a</A> Ferrarini PL. Mori C. Badawneh M. Calderone V. Calzolari L. Loffredo T. Martinotti E. Saccomanni G. Eur. J. Med. Chem.  1998,  33:  383 

<A NAME="RS02405ST-5B">5b</A> Leonard JT. Gangadhar R. Gnanasam SK. Ramachandran S. Saravanan M. Sridhar SK. Biol. Pharm. Bull.  2002,  25:  798 

<A NAME="RS02405ST-5C">5c</A> Al jamal JA. Badawneh M. Arch. Pharm. Pharm. Med. Chem.  2003,  336:  285 

<A NAME="RS02405ST-6">6</A> Che C.-M. Wan C.-W. Ho K.-Y. Zhou Z.-Y. New. J. Chem.  2001,  25:  63 

<A NAME="RS02405ST-7">7</A> Boelrijk AEM. Neenan TX. Reedijk J. J. Chem. Soc., Dalton Trans.  1997,  4561 

<A NAME="RS02405ST-8">8</A> Newkome GR. Garbis SJ. Majestic VK. Fronczek FR. Chiari G. J. Org. Chem.  1981,  46:  833 

<A NAME="RS02405ST-9">9</A> Collin J.-P. Youinou M.-T. Inorg. Chim. Acta  1992,  201:  29 

<A NAME="RS02405ST-10A">10a</A> Lee S. Jørgensen M. Hartwig JF. Org. Lett.  2001,  3:  2729 

<A NAME="RS02405ST-10B">10b</A> Huang X. Buchwald SL. Org. Lett.  2001,  3:  3417