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 2008(15): 2462-2466
DOI: 10.1055/s-2008-1067159
DOI: 10.1055/s-2008-1067159
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of 4-Hydroxy-1H-pyrrole-2,3-dicarboxylic Acid Derivatives: Unusual Coupling of Acetylenic Esters and α-Amino Acids in the Presence of Cyclohexyl Isocyanide or N,N′-Dicyclohexylcarbodiimide
Further Information
Received
3 April 2008
Publication Date:
08 July 2008 (online)
Publication History
Publication Date:
08 July 2008 (online)

Abstract
A facile and direct synthetic entry to 4-hydroxy-1H-pyrrole-2,3-dicarboxylic acid derivatives is reported. It is based on the unusual ring annulation of acetylenic esters and α-amino acids with isocyanide or carbodiimide under neutral conditions in a one-step procedure.
Key words
pyrroles - α-amino acids - alkynes - isocyanides - N,N′-dicyclohexylcarbodiimide
- 1a
Carson JR.McKinstry DN.Wong S. J. Med. Chem. 1971, 14: 646 - 1b
Stork G.Nakahara Y.Nakahara Y.Greenlee WJ. J. Am. Chem. Soc. 1978, 100: 7775 - 1c
Stork G.Nakamura E. J. Am. Chem. Soc. 1983, 105: 5510 - 1d
Bickmeyer U.Drechsler C.Köck M.Assmann M. Toxicon 2004, 44: 45 - 1e
Lindel T.Breckle G.Hochgürtel M.Volk C.Grube A.Köck M. Tetrahedron Lett. 2004, 45: 8149 - 2a
Falk H. The Chemistry of Linear Oligopyrroles and Bile Pigments Springer; Vienna: 1989. p.355 - 2b
Montforts FP.Schwartz UM. Angew. Chem., Int. Ed. Engl. 1985, 24: 775 ; Angew. Chem. 1985, 97, 767 - 2c
Dutton CJ.Fookes CJR.Battersby AR. J. Chem. Soc., Chem. Commun. 1983, 1237 - 3
Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1998, 615 - 4
Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1999, 2849 - 5
Lagu B.Pan M.Wachter MP. Tetrahedron Lett. 2001, 42: 6027 - 6
Attanasi O.Fillipone P.Perrulli FR.Santensanio S. Tetrahedron 2001, 57: 1387 - 7a
Kolar P.Tisler M. Synth. Commun. 1994, 24: 1887 - 7b
Kawashima K.Hiromoto M.Hayashi K.Kakehi A.Shiro M.Noguchi M. Tetrahedron Lett. 2007, 48: 941 - 8
Alizadeh A.Rostamnia S.Zhu LG. Tetrahedron 2006, 62: 5641 - 9a
Alizadeh A.Rostamnia S.Hu ML. Synlett 2006, 1592 - 9b
Alizadeh A.Rostamnia S.Esmaili AA. Synthesis 2007, 709 - 10
Alizadeh A.Oskueyan Q.Rostamnia S. Synthesis 2007, 2637 - 11a
Ugi I. Isonitrile Chemistry Academic Press; New York: 1971. - 11b
Shaabani A.Soleimani E.Rezayan AH. Tetrahedron Lett. 2007, 48: 6137 - 11c
Sung K.Chen CC. Tetrahedron Lett. 2001, 42: 4845 - 11d
Lim YY.Stein AR. Can. J. Chem. 1971, 49: 2455 - 11e
Alizadeh A.Movahedi F.Masrouri H.Zhu LG. Synthesis 2006, 3431 - 11f
Alizadeh A.Movahedi F.Esmaili AA. Tetrahedron Lett. 2006, 47: 4469