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Synlett 2005(9): 1435-1436
DOI: 10.1055/s-2005-868507
DOI: 10.1055/s-2005-868507
LETTER
© Georg Thieme Verlag Stuttgart · New York
Preparation of 2,7-Diamino-1,8-naphthyridine: A Useful Building Block for Supramolecular Chemistry
Further Information
Received
23 February 2005
Publication Date:
29 April 2005 (online)
Publication History
Publication Date:
29 April 2005 (online)
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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.
Key words
heterocycles - nucleophilic aromatic substitution - supramolecular systems - hydrogen bond - amine protecting group
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1a
Corbin PS.Zimmerman SC. J. Am. Chem. Soc. 1998, 120: 9710 -
1b
Corbin PS.Zimmerman SC. J. Am. Chem. Soc. 2000, 122: 3779 -
1c
Zimmerman SC.Corbin PS. Struct. Bonding 2000, 96: 63 -
1d
Corbin PS.Zimmerman SC.Thiessen PA.Hawryluk NA.Murray TJ. J. Am. Chem. Soc. 2001, 123: 10475 -
1e
Corbin PS.Lawless LJ.Li Z.-T.Ma Y.Witmer MJ.Zimmerman SC. Proc. Natl. Acad. Sci. U.S.A. 2002, 99: 5099 -
2a
Lüning U.Kühl C. Tetrahedron Lett. 1998, 39: 5735 -
2b
Brammer S.Lüning U.Kühl C. Eur. J. Org. Chem. 2002, 4054 -
2c
Lüning U.Kühl C.Uphoff A. Eur. J. Org. Chem. 2002, 4063 -
3a
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 -
3b
Zhao X.Wang X.-Z.Jiang X.-K.Chen Y.-Q.Li Z.-T.Chen G.-J. J. Am. Chem. Soc. 2003, 125: 15128 -
3c
Li X.-Q.Jiang X.-K.Wang X.-Z.Li Z.-T. Tetrahedron 2004, 60: 2063 -
3d
Li X.-Q.Feng D.-J.Jiang X.-K.Li Z.-T. Tetrahedron 2004, 60: 8275 - 4
Ligthart GBWL.Ohkawa H.Sijbesma RP.Meijer EW. J. Am. Chem. Soc. 2005, 127: 810 -
5a
Ferrarini PL.Mori C.Badawneh M.Calderone V.Calzolari L.Loffredo T.Martinotti E.Saccomanni G. Eur. J. Med. Chem. 1998, 33: 383 -
5b
Leonard JT.Gangadhar R.Gnanasam SK.Ramachandran S.Saravanan M.Sridhar SK. Biol. Pharm. Bull. 2002, 25: 798 -
5c
Al jamal JA.Badawneh M. Arch. Pharm. Pharm. Med. Chem. 2003, 336: 285 - 6
Che C.-M.Wan C.-W.Ho K.-Y.Zhou Z.-Y. New. J. Chem. 2001, 25: 63 - 7
Boelrijk AEM.Neenan TX.Reedijk J. J. Chem. Soc., Dalton Trans. 1997, 4561 - 8
Newkome GR.Garbis SJ.Majestic VK.Fronczek FR.Chiari G. J. Org. Chem. 1981, 46: 833 - 9
Collin J.-P.Youinou M.-T. Inorg. Chim. Acta 1992, 201: 29 -
10a
Lee S.Jørgensen M.Hartwig JF. Org. Lett. 2001, 3: 2729 -
10b
Huang X.Buchwald SL. Org. Lett. 2001, 3: 3417