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): 761-765
DOI: 10.1055/s-2007-965919
DOI: 10.1055/s-2007-965919
PAPER
© Georg Thieme Verlag Stuttgart · New York
3-Substituted Phthalic Acid Derivatives by Sonogashira Coupling Reaction
Further Information
Received
16 October 2006
Publication Date:
08 February 2007 (online)
Publication History
Publication Date:
08 February 2007 (online)
Abstract
Phthalic acid derivatives with carbon substituents in position 3 are easily accessible by Sonogashira coupling reaction of the corresponding bromo derivative. For reasonable conversions the phthaloyl moiety is masked as the N-phenylphthalimide, which can smoothly be converted into other phthalic acid derivatives.
Key words
alkynes - palladium - cross-coupling - heterocycles - phthalic acid
-
1a
Waldvogel SR.Fröhlich R.Schalley CA. Angew. Chem. Int. Ed. 2000, 39: 2472 -
1b
Schopohl MC.Siering C.Kataeva O.Waldvogel SR. Angew. Chem. Int. Ed. 2003, 42: 2620 -
1c
Siering C.Grimme S.Waldvogel SR. Chem. Eur. J. 2005, 11: 1877 -
1d
Schopohl MC.Faust A.Mirk D.Fröhlich R.Kataeva O.Waldvogel SR. Eur. J. Org. Chem. 2005, 2987 -
1e
Siering C.Kerschbaumer H.Nieger M.Waldvogel SR. Org. Lett. 2006, 8: 1471 -
2a
Siegl WO.Ferris FC.Mucci PA. J. Org. Chem. 1977, 42: 3442 -
2b
Larner BW.Peters AT. J. Chem. Soc. 1952, 680 -
2c
Markezich RL.Zamek OS.Donahue PE.Williams FJ. J. Org. Chem. 1977, 42: 3435 -
2d
Moore TS.Marrack MT.Proud AK. J. Chem. Soc., Trans. 1921, 119: 1786 -
2e
Märkl G.Gschwender K.Rötzer I.Kreitmeier P. Helv. Chim. Acta 2004, 87: 825 -
2f
Tajik H.Esmaeili AA.Mohmmadpoor-Baltrok I.Tajmehri H. Synth. Commun. 2003, 33: 1319 ; several other derivatives are commercially available - 3
Schaefer JP.Higgins J.Shenoy P. Org. Synth. Coll. Vol. V John Wiley & Sons; London: 1973. p.142 - 4
Soucy C.Favreau D.Kayser MM. J. Org. Chem. 1987, 52: 129 - 5
Chaudhari MB.Nargund KS. J. University Bombay, Science 1950, 18: 15 -
6a
Bräse S.de Meijere A. In Metal-Catalysed Cross-Coupling Reactions 2nd ed., Vol. 1:de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. p.217 -
6b
Marsden JA.Haley MM. In Metal-Catalysed Cross-Coupling Reactions 2nd ed., Vol. 1:de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. p.317 -
7a
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 16: 4467 -
7b
Singh R.Just G. J. Org. Chem. 1989, 54: 4453 -
7c
Uenishi J.Matsui K.Ohmiya H. J. Organomet. Chem. 2002, 653: 141 -
7d
Wan WB.Haley MM. J. Org. Chem. 2001, 66: 3893 -
7e
Novak Z.Szabo A.Repasi J.Kotschy A. J. Org. Chem. 2003, 68: 3327 -
7f
Herrmann WA.Reisinger C.-P.Speigler M. J. Organomet. Chem. 1998, 557: 93 -
8a
Avila CM.Romeiro NC.Sperandio da Silva GM.Sant’Anna CMR.Barrwiro EJ.Fraga CAM. Bioorg. Med. Chem. 2006, 14: 6874 -
8b
Noguchi T.Miyachi H.Katayama R.Naito M.Hashimoto Y. Bioorg. Med. Chem. Lett. 2005, 15: 3212 -
8c
Lepper ER.Ng SSW.Gütschow M.Weiss M.Hauschildt S.Hecker TK.Luzzio FA.Eger K.Figg WD. J. Med. Chem. 2004, 47: 2219 -
8d
Noguchi T.Shimazawa R.Nagasawa K.Hashimoto Y. Bioorg. Med. Chem. Lett. 2002, 12: 1043 -
8e
Teubert U.Zwingenberger K.Wendt S.Eger K. Arch. Pharm. (Weinheim, Ger.) 1998, 331: 7 - 9
Han L.-B.Tanaka M. J. Am. Chem. Soc. 1998, 120: 8249