Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(5): 791-793
DOI: 10.1055/s-2007-965905
DOI: 10.1055/s-2007-965905
PSP
© Georg Thieme Verlag Stuttgart · New York
An Improved Synthesis of 6,6′-Diamino-2,2′-bipyridine
Further Information
Received
19 October 2006
Publication Date:
25 January 2007 (online)
Publication History
Publication Date:
25 January 2007 (online)
Abstract
A simple synthesis for 6,6′-diamino-2,2′-bipyridine from 6,6′-dibromo-2,2′-bipyridine has been developed that does not require the use of a pressure bomb. The conversion is effected in yields of 85-95% by potassium amide in liquid ammonia with iron(III) nitrate nonahydrate as the catalyst.
Key words
amination - 2,2′-bipyridine - liquid ammonia - iron catalysis
- 1
Ogawa S.Kishii N.Shiraishi S. J. Chem. Soc., Perkin Trans. 1 1984, 2023 - 2
Costamagna J.Caruso F.Rossi M.Campos M.Canales J.Ramirez JJ. Coord. Chem. 2001, 54: 247 - 3
Schneider JP.Kelly JW. J. Am. Chem. Soc. 1995, 117: 2533 - 4
Araki K.Lee S.-K.Otsuki J. J. Chem. Soc., Dalton Trans. 1996, 1367 - 5
Ihara T.Shirasaka Y.Sato Y.Kitamura Y.Okada K.Tazaki M.Jyo A. Heterocycles 2005, 65: 293 - 6
Kojima T.Kitaguchi H.Tachi Y.Yasutake M.Naruta Y.Matsuda Y. Inorg. Chim. Acta 2005, 358: 3592 - 7
Yamada M.Araki K.Shiraishi S. Bull. Chem. Soc. Jpn. 1988, 61: 2208 - 8
Araki K.Fuse M.Kishii N.Shiraishi S.Kodama T.Uchida Y. Bull. Chem. Soc. Jpn. 1990, 63: 1299 - 9
Araki K.Fuse M.Kishii N.Shiraishi S. Bull. Chem. Soc. Jpn. 1992, 65: 1220 - 10
Araki K.Mutai T.Shigemitsu Y.Yamada M.Nakajima T.Kuroda S.Shimao I. J. Chem. Soc., Perkin Trans. 2 1996, 613 - 11
Schlaf M. Dalton Trans. 2006, 4645 - 12
Parks JE.Wagner BE.Holm RH. J. Organomet. Chem. 1973, 56: 53 - 13
Kishii N.Araki K.Shiraishi S. Bull. Chem. Soc. Jpn. 1984, 57: 2121 - 14
Schneider JP.Topgi RS.Kelly JW. Synth. Commun. 1992, 22: 1033 - 15
Moon MP.Komin AP.Wolfe JF.Morris GF. J. Org. Chem. 1983, 48: 2392 - 16
Wong J.-W.Natalie KJ.Nwokogu GC.Pisipati JS.Flaherty PT.Greenwood TD.Wolfe JF. J. Org. Chem. 1997, 62: 6152 - 17
Brandsma L.Verkruijsse H. In Preparative Polar Organometallic Chemistry 1 Springer-Verlag; Berlin: 1987. p.3-23